Process for producing L-(S) propylidene glycerin aldehyde solution

A technology of propylidene glycerol and its production method, which is applied in the field of production of L-(S)-propylidene glyceraldehyde solution, and can solve the problems of instability, high production cost and poor purity of L-(S)-propylidene glyceraldehyde. Problems, to achieve the effect of improving equipment efficiency and labor efficiency, low cost, and cost reduction

Inactive Publication Date: 2006-03-29
PORTON PHARMA SOLUTIONS LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0020] For the problems existing in the above-mentioned prior art, the object of the present invention is to overcome the defects of high production cost and poor purity of the prior art L-(S)-propylidene glyceraldehyde and solve the problem of L-(S)-propylidene glyceraldehyde. Stable technical problem, provide a kind of production method that is suitable for industrialized production L-(S)-propylidene glyceraldehyde, this method cost is low, yield is high, and the purity of produced L-(S)-propylidene glyceraldehyde is high , the chemical purity is higher than 97.5%, and the optical purity is higher than 99.9%, which can fully meet the requirements of chiral drug synthesis

Method used

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  • Process for producing L-(S) propylidene glycerin aldehyde solution
  • Process for producing L-(S) propylidene glycerin aldehyde solution
  • Process for producing L-(S) propylidene glycerin aldehyde solution

Examples

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Embodiment 1

[0032] Synthesis of L-gulonic acid-1,4-lactone

[0033] Dissolve 23.1 grams of vitamin C in 170 milliliters of water, add 2.2 grams of 5% palladium / carbon catalyst, at 50 ° C and 5.05 × 10 5 Catalyzed hydrogenation under Pa for 24 hours, filtered to remove the catalyst, and evaporated the water under reduced pressure to obtain L-gulonic acid-1,4-lactone, which was recrystallized with a mixed solvent of methanol and ethanol to obtain 22 grams of the product with a yield of 95%. , melting point 182-183.5°C; [α]- is +55.2° (c=1, H 2 O);

[0034] IR(KBr)1770cm -1 ;

[0035] 1 H-NMR (Me 2 SO-d 6 ): δ=

[0036] 5.80 (d, 1, OH), 5.30 (d, 1, OH), 4.95 (d, 1, OH) 4.45-4.07 (m, 3), 4.00-3.35 (m, 3), 4.00-3.35 (m, 3).

[0037] Synthesis of 5,6-O-isopropylidene-L-gulonic acid-1,4-lactone

[0038]Dissolve 221.6 grams of L-gulonic acid-1,4-lactone in 2000 milliliters of N,N-dimethylformamide, cool to 10°C, add 1.8 grams of p-toluenesulfonic acid while stirring, and keep the temper...

Embodiment 2

[0045] Production of L-gulonic acid-1,4-lactone

[0046] Dissolve 200 kg of vitamin C in 1000 liters of water, add 20 kg of 10% palladium / carbon catalyst, at 50 ° C and 5.05 × 10 5 Catalytic hydrogenation under Pa for 24 hours, remove the catalyst by filtration, distill off the water under reduced pressure to obtain a white solid which is the crude product of L-gulonic acid-1,4-lactone, which is recrystallized with a mixed solvent of methanol and ethanol to obtain a white cube Crystalline L-gulonic acid-1,4-lactone 196 kg, yield 98%, melting point 183-183.5°C, [a] 25 is +55.5° (c=1, H 2 O).

[0047] Synthesis of 5,6-O-isopropylidene-L-gulonic acid-1,4-lactone

[0048] Dissolve 190 kg of L-gulonic acid-1,4-lactone in 1500 liters of DMF, cool to 10°C, add 1.8 kg of p-toluenesulfonic acid while stirring, and add 2,2-dimethyl dropwise while keeping the temperature below 10°C 150 kg of oxypropane, continue to stir at room temperature for 24 hours, then add 220 kg of sodium carb...

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Abstract

The present invention produces L-(S)-propylidene glycerin aldehyde solution with vitamin C as material and through the following steps: high pressure catalytic hydrogenation, hydroxy protection, oxidation with sodium periodate in oxidation system. The present invention features that the production process also includes dissolving L-(S)-propylidene glycerin aldehyde in organic solvent to obtain L-(S)-propylidene glycerin aldehyde solution, and that mixed organic solvent and water as oxidation system is used. The L-(S)-propylidene glycerin aldehyde solution has stable performance, low cost, high chemical product purity and optical product purity higher than 99.9 %, and may be used in synthesizing chiral medicine; and the process may be used in industrial production.

Description

technical field [0001] The invention relates to a production method of propylene glycol aldehyde solution, in particular to a production method of L-(S)-propylene glycol aldehyde solution (L-(S)-Glyceraldehyde Acetonide Solution). Background technique [0002] Propylglyceraldehyde is an important intermediate in organic synthesis, which plays an important role in the synthesis of medicine and agricultural chemicals. Since propylidene glyceraldehyde has a chiral carbon atom, it has a pair of enantiomers: L-(S)-propylidene glyceraldehyde and L-(R)-propylidene glyceraldehyde, and the molecular structure is shown in the figure. [0003] [0004] L-(S)-Propylglyceraldehyde L-(R)-Propylglyceraldehyde [0005] Optically pure propylidene glyceraldehyde can be used as a chiral source for asymmetric synthesis in organic synthesis, especially because it contains an active functional group-aldehyde group, which can be connected to a variety of compounds, so it is very useful in the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/26
Inventor 冰青
Owner PORTON PHARMA SOLUTIONS LTD
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