Methanol → Methyl 2-amino-3-(3,4-dichlorophenyl)propanoate hydrochloride

HRID 2265166Notes

Reaction equation

C(OC([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)[C:10]([OH:12])=[O:11])=O)(C)(C)C.O=S(Cl)Cl.[CH3:26]O>>[ClH:20].[CH3:26][O:12][C:10](=[O:11])[CH:9]([NH2:8])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 2734501(2S)-2-(((tert-butoxy)carbonyl)amino)-3-(3,4-dichlorophenyl)propanoic acid

Product 1

HCID 68772138Methyl 2-amino-3-(3,4-dichlorophenyl)propanoate hydrochlorideYield 99%

Procedure

To a stirred solution of (S)-2-tert-butoxycarbonylamino-3-(3,4-dichloro-phenyl)-propionic acid (0.67 g, 2.00 mmol) in MeOH (13 mL) at 0° C. was added SOCl2 (0.29 mL, 4.00 mmol). The reaction mixture was allowed to stir and warm to rt overnight. The mixture was concentrated to provide the product as a white solid (0.56 g, 99%). 1H NMR (400 MHz, DMSO-d6): 8.66 (br s, 2H), 7.65-7.60 (m, 2H), 7.26 (dd, J=8.2, 1.9, 1H), 4.37 (br s, 1H), 3.72 (s, 3H), 3.18-3.14 (m, 2H).

Workup

concentrationThe mixture was concentrated

Sources & evidence

ORD record: ord-811a41036288466cbe1e4b1961fdc74d
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855292B2

Reaction notes

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