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Method for preparing D-biotin intermediate

A compound and mixture technology, applied in the field of preparation of thiolactone compounds, can solve problems such as trouble, affecting the yield and purity of thiolactone compounds, instability of potassium thioacetate, etc., and achieve high-purity effects

Pending Publication Date: 2022-07-29
DSM IP ASSETS BV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, potassium thioacetate is unstable under the reaction conditions, thus adversely affecting the yield and purity of the obtained thiolactone compound (b)
In addition, the impurity of the thiolactone compound (b) may cause trouble in the following steps for the production of biotin

Method used

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  • Method for preparing D-biotin intermediate
  • Method for preparing D-biotin intermediate
  • Method for preparing D-biotin intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038]

[0039] In a 250 mL four-necked flask equipped with a thermometer, stirrer, condenser and nitrogen vent and supported in a thermo-statically controlled oil bath, charged with 12.50 g of (+)-lactone 2 and 7 mL of DMF, and heated to an internal temperature of 145°C.

[0040] Under nitrogen atmosphere, 7.51 g of potassium thiobenzoate was dissolved in 17 mL of DMF. While maintaining an internal temperature of 145°C, the potassium thiobenzoate solution was quickly transferred to the flask. An additional 2 mL of DMF was added to ensure complete transfer.

[0041] After stirring at 145°C for 60 minutes, the obtained mixture was cooled to about 50°C and then 56 mL of toluene was added. After stirring for an additional 5 minutes, the mixture was transferred to a separatory funnel containing 108 mL of water. An additional 67 mL of toluene was added to complete the transfer.

[0042]The funnel containing the two layers was shaken, then the lower aqueous phase was separate...

Embodiment 2

[0044]

[0045] In a 250 mL four-necked flask equipped with a thermometer, stirrer, condenser and nitrogen vent and supported in a thermostatically controlled oil bath, 12.50 g of (+)-lactone 2 and 7 mL of NMP were charged and heated to 145°C internal temperature.

[0046] Under nitrogen atmosphere, 7.51 g of potassium thiobenzoate was dissolved in 17 mL of NMP. While maintaining an internal temperature of 145°C, the potassium thiobenzoate solution was quickly transferred to the flask. An additional 2 mL of NMP was added to ensure complete transfer.

[0047] After stirring at 145°C for 60 minutes, the obtained mixture was cooled to about 50°C and then 56 mL of toluene was added. After stirring for an additional 5 minutes, the mixture was transferred to a separatory funnel containing 108 mL of water. An additional 67 mL of toluene was added to complete the transfer.

[0048] The funnel containing the two layers was shaken, then the lower aqueous phase was separated into ...

Embodiment 3

[0050]

[0051] In a 250 mL four-necked flask equipped with a thermometer, stirrer, condenser and nitrogen vent and supported in a thermostatically controlled oil bath, charged with 12.50 g of (+)-lactone 2 and 7 mL of DEF and heated to 145°C internal temperature.

[0052] Under nitrogen atmosphere, 7.51 g of potassium thiobenzoate was dissolved in 17 mL of DEF. While maintaining an internal temperature of 145°C, the potassium thiobenzoate solution was quickly transferred to the flask. An additional 2 mL of DEF was added to ensure complete transfer.

[0053] After stirring at 145°C for 60 minutes, the obtained mixture was cooled to about 50°C and then 56 mL of toluene was added. After stirring for an additional 5 minutes, the mixture was transferred to a separatory funnel containing 108 mL of water. An additional 67 mL of toluene was added to complete the transfer.

[0054] The funnel containing the two layers was shaken, then the lower aqueous phase was separated into ...

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Abstract

The present invention provides a process for the preparation of a thiolactone compound of formula (I) wherein R and R'are independently H, lower alkyl, aryl or acyl groups, which R and R 'are optionally substituted with one or more substituents, or geometric isomers thereof or mixtures thereof. According to the present invention, the process surprisingly provides a stable reaction that results in higher purity and / or yield compared to the process of the prior art.

Description

technical field [0001] The present invention relates to a method for preparing thiolactone compounds, which are important intermediates for preparing D-biotin. Background technique [0002] D-biotin, also known as vitamin H, is mainly used in the fields of medicine and hygiene, nutritional supplements, feed additives, cosmetics and beverages. The molecular structure of D-biotin is as follows: [0003] [0004] Since the first industrial synthesis of D-biotin by the Swiss company Roche in 1949, this synthesis method still has many studies in the world. To date, there have been many reports on the total synthetic route. However, the most industrial method for D-biotin is to use a lactone compound (a) to prepare a thiolactone compound (b), which is then ultimately converted to D-biotin (see US 3,740,416). [0005] [0006] In this US Patent Publication, the thiolactone compound (b) is prepared by reacting the lactone compound (a) with a salt of a thio derivative of a ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04
CPCC07D495/04C07B2200/07
Inventor 维尔纳·邦拉蒂高搏拉尔法·哈尔特托马斯·麦克·唐纳德·麦克莱蒙克劳迪娅·尼奇克彭坤张琼梅
Owner DSM IP ASSETS BV
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