Supercharge Your Innovation With Domain-Expert AI Agents!

Synthesis method of 17-alpha-hydroxy steroid compounds

A technology of hydroxysteroids and synthetic methods, applied in the direction of steroids, chemical instruments and methods, organic chemistry, etc., can solve problems such as unrealized methods, avoid protection/deprotection process, increase applicable surface, and mild reaction conditions Effect

Inactive Publication Date: 2015-04-29
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
View PDF1 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Selective removal is possible if formyl groups are used, but not possible with reported methods

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthesis method of 17-alpha-hydroxy steroid compounds
  • Synthesis method of 17-alpha-hydroxy steroid compounds
  • Synthesis method of 17-alpha-hydroxy steroid compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Synthesis of Example 1 Fluorosulfonate 2

[0044]

[0045] The commercial compound 1 (947mg, 2.52mmol) was dissolved in 20mL of toluene, cooled in an ice bath, and DBU (0.90mL, 6.0mmol) and C 4 f 9 SO 2 F (0.54mL, 3.0mmol), the reaction was completed in about 10 minutes, poured into a short silica gel column, and washed with petroleum ether: ethyl acetate: dichloromethane = 10:1:1 to obtain about 1.58 g Product 2, yield 96%.

[0046] m.p.110℃

[0047] [α] D 25 =+7.33(c 1.0, CHCl 3 )

[0048] 1 H NMR (400MHz, CDCl3 )δ8.20(d, J=7.9Hz, 2H), 7.63(t, J=7.0Hz, 1H), 7.51(t, J=7.6Hz, 2H), 7.33(d, J=8.4Hz, 1H) ,6.99(d,J=8.5Hz,1H),6.94(s,1H),4.89(t,J=8.4Hz,1H),0.95(s,3H).

[0049] 19 F NMR (376MHz, CDCl 3 )δ-80.71(t,J=9.7Hz,3F),-111.26(dd,J=27.0,18.4Hz,2F),-121.26(d,J=9.0Hz,2F),-125.86–-126.09(m ,2F).

[0050] 13 C NMR (101MHz, CDCl 3 )δ165.4, 148.8, 138.0, 137.2, 133.5, 130.1, 129.6, 128.5, 126.5, 121.7, 118.9, 97.7, 48.6, 43.8, 43.7, 38.2, 35.9, 29.4, 27.8, 2...

Embodiment 21

[0051] Example 2 Synthesis of 17-α-hydroxyacetate 3

[0052]

[0053] Intermediate 2 (240mg, 0.36mmol) was dissolved in 3mL of toluene, acetic acid (83μL, 1.46mmol) and DBU (218μL, 1.46mmol) were added, and the reaction was completed after 0.5 hours. 3 Aqueous solution, saturated NH 4 Cl aqueous solution and saturated brine washing, anhydrous Na 2 SO 4 After drying, concentration and column chromatography. 3122 mg of the product was obtained with a yield of 80%.

[0054] m.p.148–149°C

[0055] [α] D 25 =+32.76(c 1.0, CHCl 3 )

[0056] 1 H NMR (400MHz, CDCl 3 )δ8.20(d, J=7.5Hz, 2H), 7.62(d, J=7.4Hz, 1H), 7.51(t, J=7.7Hz, 2H), 7.34(d, J=8.5Hz, 1H) ,6.98(d,J=8.4Hz,1H),6.94(s,1H),4.89(d,J=6.2Hz,1H),2.07(s,3H),0.80(s,3H).

[0057] 13 C NMR (101MHz, CDCl 3 )δ170.7, 165.4, 148.7, 138.3, 138.0, 133.4, 130.1, 129.7, 128.5, 126.5, 121.6, 118.7, 82.0, 49.1, 44.9, 43.8, 38.6, 31.8, 30.1, 29.6, 267.8, 33.2.0, 2 .

Embodiment 31

[0058] Example 3 Synthesis of 17-alpha-hydroxyformic acid ester 4

[0059]

[0060] The starting material (240 mg, 0.36 mmol) was dissolved in 3 mL of tetrahydrofuran, formic acid (55 μL, 1.46 mmol) and DBU (218 μL, 1.46 mmol) were added, and the reaction was completed after 0.5 hours. 3 Aqueous solution, saturated NH 4 Cl aqueous solution and saturated brine washing, anhydrous Na 2 SO 4 After drying, concentration and column chromatography. 3113 mg of the product was obtained with a yield of 78%.

[0061] [α] D 25 =+48.12(c 1.0, CHCl 3 ).

[0062] 1 H NMR (400MHz, CDCl 3 )δ8.20(d, J=7.5Hz, 2H), 7.62(d, J=7.4Hz, 1H), 7.51(t, J=7.7Hz, 2H), 7.34(d, J=8.5Hz, 1H) ,6.98(d,J=8.4Hz,1H),6.94(s,1H),4.89(d,J=6.2Hz,1H),2.07(s,3H),0.80(s,3H).

[0063] 13 C NMR (101MHz, CDCl 3 )δ165.4, 160.8, 148.7, 138.2, 137.8, 133.4, 130.1, 129.7, 128.5, 126.5, 121.6, 118.7, 81.9, 49.0, 44.9, 43.7, 38.6, 31.9, 30.1, 29.6, 27.8, 25.9, 2

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides a synthesis method of 17-alpha-hydroxy steroid compounds. Fluoroalkyl sulfuryl fluoride is used as an activating reagent to reverse the hydroxy group of the 17-alpha-hydroxy steroid compounds so as to efficiently introduce the 17-alpha-hydroxy which can not be easily synthesized by the conventional process. The structural formula of the D ring of the 17-alpha-hydroxy steroid compounds (I) is disclosed in the specification, wherein R is hydrogen, formacyl group, acetyl group, benzoyl group or trifluoroacetyl group. The 17-alpha-hydroxy steroid compounds can not be easily synthesized by the conventional process, or the synthesis route is lengthy. The method has the advantages of short synthesis route and wide application range of the substrate, and can be used for efficiently and quickly synthesizing the 17-alpha-hydroxy steroid compounds.

Description

technical field [0001] The invention relates to a synthesis method of 17-alpha-hydroxy steroid compounds, which can efficiently synthesize some 17-alpha-hydroxy steroid compounds which are difficult to synthesize by conventional methods. Background technique [0002] Steroids are endogenous hormones that widely exist in the human body, animals, plants, and microorganisms, and participate in and control the growth and development of the human body, animals, plants, and insects. Steroids are widely used in the treatment of rheumatoid arthritis, heart disease, Alzheimer's disease, lupus erythematosus, angiogenesis, tumors and other diseases, and are used as contraceptives in controlling excessive population growth. [0003] When steroid hormones enter specific cells (these cells are called target cells), specific receptor proteins in the cells combine with them to form hormone-receptor complexes, thereby regulating gene expression and protein biosynthesis. The configuration of...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07J1/00C07J75/00
CPCC07J1/0018C07J1/0025C07J75/00
Inventor 丁凯郭朋朋
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com