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

HRID 852004Notes

Reaction equation

HRID 852004 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[C@@H:14]2[CH2:20][C:19]([CH3:22])([CH3:21])[CH2:18][CH2:17][NH:16][C:15]2=[O:23])=[CH:8][CH:7]=1.[OH-].[Na+]>CO.O>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([S:24]([N:13]([CH2:12][C:9]2[CH:8]=[CH:7][C:6]([CH2:5][CH2:4][C:3]([OH:34])=[O:2])=[CH:11][CH:10]=2)[C@@H:14]2[CH2:20][C:19]([CH3:21])([CH3:22])[CH2:18][CH2:17][NH:16][C:15]2=[O:23])(=[O:25])=[O:26])=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 115117683-(4-{[(4-chloro-benzenesulfonyl)-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-amino]-methyl}-phenyl)-propionic acid methyl ester

Product 1

HCID 115188373-(4-{[(4-Chloro-benzenesulfonyl)-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-amino]-methyl}-phenyl)-propionic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-(4-{[(4-Chloro-benzenesulfonyl)-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-amino]-methyl}-phenyl)-propionic acid methyl ester (0.06 g, 0.11 mmol) was dissolved in methanol (4 ml) and treated with 1 N NaOH (0.2 ml) overnight. The mixture was diluted with water and the methanol removed under reduced pressure. The residue was acidified (KHSO4/K2SO4) and extracted with ethyl acetate (3×). The combined extracts were concentrated and the crude residue was purified using preparative RP(C18) chromatography: lyophilisate 15 mg; MS: m/e=491.1 (MH+).

Workup

  1. customthe methanol removed under reduced pressure
  2. extractionextracted with ethyl acetate (3×)
  3. concentrationThe combined extracts were concentrated
  4. customthe crude residue was purified

Sources & evidence

ORD record
ord-4b4b631fc7f74469af07d249202e3c90
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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