p-Bromobenzenesulfonyl chloride → 4-Bromo-N-[(1R,2R)-1-(hydroxymethyl)-2-methylbutyl]benzenesulfonamide

HRID 1375192

Reaction equation

HRID 1375192 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.ClC1C=CC(S(Cl)(=O)=O)=CC=1.[NH2:23][C@@H:24]([C:29](O)=[O:30])[C@@H:25]([CH2:27][CH3:28])[CH3:26].CC([C@](N)(C(O)=O)C)C.CC(C1C=CC=CC=1)C(C(O)=O)N.N[C@H](C(O)=O)[C@@H](CC)C>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:23][C@@H:24]([CH2:29][OH:30])[C@H:25]([CH3:26])[CH2:27][CH3:28])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 6

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 73984-Chlorobenzenesulfonyl chlorideHCID 648082-Amino-3-phenylbutanoic acidHCID 76551D-IsoleucineHCID 99288Alloisoleucine, DL-HCID 7408715(S)-2-amino-2,3-dimethylbutanoic acid

Product 1

HCID 103370674-Bromo-N-[(1R,2R)-1-(hydroxymethyl)-2-methylbutyl]benzenesulfonamide

Procedure

The following compounds (Examples 33–39, Table 5) were prepared using 4-bromobenzenesulfonyl chloride, and 4-chlorobenzenesulfonyl chloride, with D-isoleucine, L-α-methyl-valine, β-methyl-DL-phenylalanine, and L-allo-isoleucine and following the procedure outlined in Example 33. This procedure is outlined in the following Scheme.

Workup

  1. customThe following compounds (Examples 33–39, Table 5) were prepared

Sources & evidence

ORD record
ord-584039e801454c479c6577ce1f234983
Source dataset
uspto-grants-2007_01
Patent number
US07166622B2

Linked notes

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