Sodium Hydroxide → 4-{[(4-chloro-benzenesulfonyl)-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-benzoic acid

HRID 852005Notes

Reaction equation

HRID 852005 reaction equation
C[O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([S:22]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[C@@H:12]2[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][CH2:15][NH:14][C:13]2=[O:21])=[C:6]([F:32])[CH:5]=1.[OH-].[Na+]>C1COCC1>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([S:22]([N:11]([CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:33])=[O:2])=[CH:5][C:6]=2[F:32])[C@@H:12]2[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][CH2:15][NH:14][C:13]2=[O:21])(=[O:23])=[O:24])=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 114969494-{[(4-chloro-benzenesulfonyl)-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-benzoic acid methyl ester

Product 1

HCID 117127634-{[(4-chloro-benzenesulfonyl)-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-{[(4-Chloro-benzenesulfonyl)-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-benzoic acid methyl ester (0.52 g, 1.1 mmol) was dissolved in THF (20 ml) and treated with 1 N NaOH (2.1 ml) for 2 h. Work-up as for Example 187 yielded crude which was crystallised from acetonitrile to give 4-{[(4-chloro-benzenesulfonyl)-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-benzoic acid: 0.38 g; MS: m/e=481.1 (MH+).

Workup

  1. customyielded crude which
  2. customwas crystallised from acetonitrile

Sources & evidence

ORD record
ord-2beed140bf4e4215b56bfe71ec33b480
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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