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

HRID 1783399ノート

反応式

HRID 1783399 の反応式
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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

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;

後処理

  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

出典と根拠

ORDレコード
ord-c961f12561c042328103a558b7a58f69
出典データセット
uspto-grants-2009_03
特許番号
US07501406B2

反応ノート

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