4-Chlorobenzenesulfonyl chloride → tert-butyl (2R)-2-{[(4-chloro-2-nitrophenyl)sulfonyl]amino}butanoate

HRID 554779Notes

Reaction equation

HRID 554779 reaction equation
Cl.[C:2]([O:6][C:7](=[O:11])[C@H:8]([CH3:10])[NH2:9])([CH3:5])([CH3:4])[CH3:3].Cl[C:13]1C=CC(S(Cl)(=O)=O)=CC=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[C:26]([N+:34]([O-:36])=[O:35])[CH:25]=1>>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([NH:9][C@H:8]([CH2:10][CH3:13])[C:7]([O:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:11])(=[O:32])=[O:31])=[C:26]([N+:34]([O-:36])=[O:35])[CH:25]=1

Participants

4

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 206314-Chloro-2-nitrophenylsulfonyl chlorideHCID 11275390tert-Butyl alaninate hydrochloride

Product 1

HCID 66935149tert-butyl (2R)-2-{[(4-chloro-2-nitrophenyl)sulfonyl]amino}butanoate

Procedure

Instead of the starting material compound of Reference Example 166, that is, L-alanine tert-butyl ester hydrochloride, D-2-amino-n-butyric acid tert-butyl ester hydrochloride was used, further, instead of 4-chlorobenzenesulfonyl chloride, 4-chloro-2-nitrobenzenesulfonyl chloride was used for the similar procedure as with Reference Example 167 to obtain the title compound.

Sources & evidence

ORD record
ord-bdebd218093e4411a1b8438629a1a95e
Source dataset
uspto-grants-2011_11
Patent number
US08049006B2

Reaction notes

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