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

HRID 1783399Notes

Reaction equation

HRID 1783399 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]([F:20])([F:19])[CH2:16][CH2:15][NH:14][C:13]2=[O:21])=[C:6]([F:32])[CH:5]=1.[OH-].[Na+]>C1COCC1.CO>[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]([F:19])([F:20])[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 686233434-{[(4-chloro-benzenesulfonyl)-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-benzoic acid methyl ester

Product 1

HCID 686243374-{[(4-Chloro-benzenesulfonyl)-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-benzoic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

4-{[(4-Chloro-benzenesulfonyl)-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-benzoic acid methyl ester (130 mg, 0.26 mmol) was dissolved in THF/MeOH (5 ml) and treated with 1 N NaOH (1.2 ml) for 1.5 h. The reaction mixture was concentrated under reduced pressure diluted using water and extracted with diethyl ether. The aqueous phase was acidified using a 5% KHSO4/10% K2SO4 mixture and extracted with ethyl acetate (3×). The combined organic fractions were washed with brine, dried (Na2SO4), filtered, concentrated under reduced pressure (103 mg). Crude product (50 mg) was purified using preparative RP(C18) chromatography: lyophilisate 22 mg;

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted
  3. extractionextracted with diethyl ether
  4. extractionextracted with ethyl acetate (3×)
  5. washThe combined organic fractions were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure (103 mg)
  9. customCrude product (50 mg) was purified

Sources & evidence

ORD record
ord-c961f12561c042328103a558b7a58f69
Source dataset
uspto-grants-2009_03
Patent number
US07501406B2

Reaction notes

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