ChemicalBook CAS DataBase List (S)-ACETYLAMINO-CYCLOHEXYL-ACETIC ACID

(S)-ACETYLAMINO-CYCLOHEXYL-ACETIC ACID synthesis

11synthesis methods

Product Name:(S)-ACETYLAMINO-CYCLOHEXYL-ACETIC ACID
CAS Number:78781-84-7
Molecular formula:C10H17NO3
Molecular Weight:199.25

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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