4-Chloro-N-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-benzenesulfonamide → 3-(2-{[(4-chloro-benzenesulfonyl)-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-amino]-methyl}-5-fluoro-phenyl)-propionic acid

HRID 852007Notes

Reaction equation

HRID 852007 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]2[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][CH2:15][NH:14][C:13]2=[O:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C[O:23][C:24](=[O:36])[CH2:25][CH2:26][C:27]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=1[CH2:34]Br>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:34][C:28]2[CH:29]=[CH:30][C:31]([F:33])=[CH:32][C:27]=2[CH2:26][CH2:25][C:24]([OH:36])=[O:23])[C@@H:12]2[CH2:18][C:17]([CH3:19])([CH3:20])[CH2:16][CH2:15][NH:14][C:13]2=[O:21])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 694892204-Chloro-N-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-benzenesulfonamideHCID 694913573-(2-Bromomethyl-5-fluoro-phenyl)-propionic acid methyl ester

Product 1

HCID 694892253-(2-{[(4-chloro-benzenesulfonyl)-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-amino]-methyl}-5-fluoro-phenyl)-propionic acid

Procedure

4-Chloro-N-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-benzenesulfonamide was alkylated using 3-(2-bromomethyl-5-fluoro-phenyl)-propionic acid methyl ester analogous to Example 2c and then saponified to give 3-(2-{[(4-chloro-benzenesulfonyl)-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-amino]-methyl}-5-fluoro-phenyl)-propionic acid. MS: m/e=509.3 (MH−).

Sources & evidence

ORD record
ord-4d599c02badb41128f0e77b6ac70d017
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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