3-Chlorobenzaldehyde → (S)-4-[(E)-2-(3-Chloro-phenyl)-vinyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

HRID 1911554Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13]S(C2SC3C=CC=CC=3N=2)(=O)=O)[CH2:11][O:10][C:9]1([CH3:27])[CH3:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH:32]=O>>[C:1]([O:5][C:6]([N:8]1[C@@H:12](/[CH:13]=[CH:32]/[C:31]2[CH:34]=[CH:35][CH:36]=[C:29]([Cl:28])[CH:30]=2)[CH2:11][O:10][C:9]1([CH3:26])[CH3:27])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 2

HCID 114773-Chlorobenzaldehyde

HCID 59173188(R)-4-(benzothiazole-2-sulfonylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 68714272(S)-4-[(E)-2-(3-Chloro-phenyl)-vinyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Procedure

In analogy to example 83c. from (R)-4-(benzothiazole-2-sulfonylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester and 3-chloro-benzaldehyde. Off-white solid. MS (ISP): 340.2 ([{37Cl}M+H]+), 338.2 ([{35Cl}M+H]+).

Sources & evidence

ORD record: ord-c6a05b232cc644199aa52c742aa0e156
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604061B2

Reaction notes

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