(S)-ACETYLAMINO-CYCLOHEXYL-ACETIC ACID synthesis
- Product Name:(S)-ACETYLAMINO-CYCLOHEXYL-ACETIC ACID
- CAS Number:78781-84-7
- Molecular formula:C10H17NO3
- Molecular Weight:199.25
Yield:-
Reaction Conditions:
with sodium hydroxide in water at 0; for 2 h;
Steps:
A28.a
L-5oc-cyclohexylglycine (0.500 g, 1.94 mmol) was dissolved in DCM (5 mL) and cooled to 0 °C. TFA (5 mL) was added and the reaction was stirred for 30 min. The mixture was concentrated in vacuo and the residue was resuspended in a few mL of toluene and the mixture evaporated by rotary evaporation (process repeated thrice) followed by drying under vacuum. The crude TFA salt was dissolved in H20 (6 mL), cooled to 0 °C and NaOH (776 mg, 19.4 mmol) was added. Stirring was continued until a homogeneous solution was achieved. Acetic anhydride (3.88 mmol, 0.388 mL) was added and the reaction was stirred for 2 h. The mixture was diluted with 1 M NaOH (25 mL) and the resulting solution was washed with Et20, then acidified with 3 M HC1 to pH = 1, and extracted with EtOAc (3 X 20 mL). The combined organic phases were dried (MgSC^), filtered and evaporated to give 120 mg of the title compound in high purity. LC-MS ES+ 200.2 [M+H]+.
References:
WO2011/70541,2011,A1 Location in patent:Page/Page column 42-43
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