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215523-07-2

CBZ-L-CYCLOPROPYL-ALA-OH synthesis

2synthesis methods
-

Yield:215523-07-2 58%

Reaction Conditions:

Stage #1: benzyl chloroformate;(2S)-2-amino-3-cyclopropylpropanoic acidwith sodium hydroxide at 20;
Stage #2: with hydrogenchloride in water monomer;

Steps:

80.1

(S)-2-amino-3-cyclopropylpropanoic acid (1.0 g, 7.743 mmol) in INNaOH (26 mL) was treated with benzyl chlorofomate (1.326 mL, 9.291 mmol) and stirred at ambient temperature overnight. This mixture was extracted with DCM, organics discarded, aqueous layer acidified with concentrated HCl and extracted with DCM. The combined organic layer was dried (phase separator silicone treated filter paper) and solvent concentrated to afford (S)-2-(benzyloxycarbonylamino)-3-cyclopropylpropanoic acid (1.18 g, 58% yield) as a white gum.

References:

WO2011/29027,2011,A1 Location in patent:Page/Page column 116; 117