Methanol → methyl (2S)-2-amino-3-cyclohexylpropanoate hydrochloride

Reaction equation

[CH:1]1([CH2:7][C@@H:8]([C:10]([OH:12])=[O:11])[NH2:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:15])=O.[CH3:17]O>>[ClH:15].[CH3:17][O:11][C:10](=[O:12])[C@H:8]([CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[NH2:9]

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 7124213-Cyclohexyl-L-alanine

Product 1

HCID 22861687methyl (2S)-2-amino-3-cyclohexylpropanoate hydrochlorideYield 83.9%

Procedure

This was synthesised according to Standard Procedure 1, using 3-cyclohexyl-L-alanine (3.0 g, 17.5 mmol), methanol (30 ml), and thionyl chloride (2.56 ml, 35 mmol). The product was isolated as a white solid (3.23 g, 83.9%).

Workup

customThis was synthesised

Sources & evidence

ORD record: ord-d89c85505f1045d3961ffc1bf3b0720d
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06638919B2

Reaction notes

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