Thionyl Chloride → (r)-Ethyl 3-amino-3-(3-nitrophenyl)propanoate hydrochloride salt

Reaction equation

Cl.[NH2:2][C@H:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].N[C@H](C1C=CC=C([N+]([O-])=O)C=1)CC(O)=O.S(Cl)([Cl:36])=O>>[ClH:36].[NH2:2][C@@H:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

Reactant 3

HCID 24386Thionyl Chloride

HCID 706689(s)-3-Amino-3-(3-nitrophenyl)propionic acid

HCID 86614935(s)-Ethyl 3-amino-3-(3-nitrophenyl)propanoate hydrochloride salt

Product 1

HCID 86614936(r)-Ethyl 3-amino-3-(3-nitrophenyl)propanoate hydrochloride saltYield 99%

Procedure

Using a procedure analogous to that used to prepare 34A, (S)-3-amino-3-(3-nitrophenyl)propanoic acid (2.1 g, 10 mmol) was reacted with thionyl chloride to 10 afford 39A (2.75 g, 99%) as a white solid. MS (ESI) m/z 239.08 (M+H)+.

Sources & evidence

ORD record: ord-6ec1eb1c0c554cf7884ae5f25c3215da
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592331B2

Reaction notes

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