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ChemicalBook CAS DataBase List Glycocholic acid
475-31-0

Glycocholic acid synthesis

6synthesis methods
-

Yield:475-31-0 92.3%

Reaction Conditions:

Stage #1: ethyl glycocholatewith lithium hydroxide monohydrate;sodium hydroxide at 20 - 28;
Stage #2: with hydrogenchloride in lithium hydroxide monohydrate; pH=7 - 7.5;

Steps:

3

Example 3Hydrolysis and precipitation of GCAAdded into a clean and dry 1 -litre glass flask are:- water 189 ml- NaOH 1.89 gStirring is carried out for about 1 hour in such a manner that all the sodium hydroxide dissolves, at ambient temperature.Once the solution is complete, 16.9 g of purified wet GCAEE are added and the suspension is stirred for about 12 hours, at a temperature comprised between 20 and 28°C.Then, the clear solution is taken to a pH comprised between 7.0 and 7.5 with about 50ml of HCl IN. The aqueous solution is washed twice using ethyl acetate75 ml, at a temperature between 35 and 40 °C.Thus, the separated aqueous solution is heated under vacuum to eliminate the ethyl acetate. The aqueous solution thus obtained is diluted with 100 ml of water, and the pure GCA is obtained by heating the solution between 35 and 40 °C and precipitation with HCl IN, up to a pH comprised between 2.0 and 2.5.The wet product is dried under vacuum between 50 and 60° C.The dry yield of the sesquihydrate product is 14 g, equivalent to 92.3% stoichiometric.TLC purityCA lower than 0.4 % - GGCAEE lower than 0.1 % - Other impurities lower than0.2 % in total. Glycine not observable.

References:

WO2010/128472,2010,A1 Location in patent:Page/Page column 6

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