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196862-32-5

L-Threonine, N-(phenylmethyl)-, methyl ester synthesis

2synthesis methods
39994-75-7 Synthesis
Methyl L-threoninate hydrochloride

39994-75-7
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L-Threonine, N-(phenylmethyl)-, methyl ester

196862-32-5
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Yield:196862-32-5 52%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in dichloromethane at 20;

Steps:

38.1 Step 1. Synthesis of Intermediate Compound 192

To a solution of compound 190 (5.3 g, 21.48 mmol) and compound 191 (2.1, 19.53 mmol) in DCM (20 mL), was added DIPEA (7.56 g, 58.58 mmol). The resulting mixture was stirred at room temperature overnight. Then to the mixture was added NaBH4 (0.82 g, 21.48 mmol). The resulting mixture was stirred for 4 h. The crude mixture was quenched with aq. NH4CI (50 mL) and extracted with ethyl acetate (200 mL x 2). The combined organic phase was washed with brine, dried over anhydrous Na2SC>4, filtrated and concentrated to dryness. The residue was purified by silica gel column (PE : EA = 10 : 1) to give title compound 192, (2S,3R)-methyl 2- (benzylamino)-3-hydroxybutanoate (2.5 g, 52% yield). LC-MS (LC method 1): m/z 224 (M+l)+.

References:

WO2017/189866,2017,A1 Location in patent:Paragraph 0231