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Water → 2-[[(1,1'-biphenyl)-4-yl]sulfonyl]amino-4-hydroxy-5-(phenylthio)-pentanoic Acid

HRID 1884279
ノート
印刷プレビュー

反応式

HRID 1884279 の反応式
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([S:7]([NH:10][CH:11]([CH2:16][CH:17]2[O:19][CH2:18]2)[C:12]([O:14]C)=[O:13])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:26]1(C2C=CC=CC=2)[CH:31]=[CH:30][C:29]([S:32](NC(CC=C)C(OC)=O)(=O)=O)=[CH:28][CH:27]=1.O.ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:1]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:6]=[CH:5][C:4]([S:7]([NH:10][CH:11]([CH2:16][CH:17]([OH:19])[CH2:18][S:32][C:29]2[CH:30]=[CH:31][CH:26]=[CH:27][CH:28]=2)[C:12]([OH:14])=[O:13])(=[O:8])=[O:9])=[CH:3][CH:2]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 23508251Methyl 2-[[(1,1'-biphenyl)-4-yl]sulfonyl]amino-4,5-epoxypentanoateHCID 23508264Methyl 2-[[(1,1'-biphenyl)-4-yl]sulfonyl]amino-4-pentenoate

生成物 1

HCID 235082932-[[(1,1'-biphenyl)-4-yl]sulfonyl]amino-4-hydroxy-5-(phenylthio)-pentanoic Acid

試薬・触媒・溶媒 2

HCID 6344
Dichloromethane
溶媒
HCID 516892Sodium Bicarbonate溶媒2 回

実験手順

Methyl 2-[[(1,1′-biphenyl)-4-yl]sulfonyl]amino-4,5-epoxypentanoate: To a solution of methyl 2-[[(1,1′-biphenyl)-4-yl]sulfonyl]amino-4-pentenoate 16a (2.0 g, 5.8 mmol) in CH2Cl2 (15 mL), NaHCO3 (0.58 g, 7 mmol) and water (10 mL) at 0° C., is added slowly m-chloroperbenzoic acid (3.3 g, 11.6 mmol, 57-86%). The reaction mixture is stirred overnight. The resulting mixture is diluted with aqueous NaHCO3, and the mixture is extracted three times with CH2Cl2. The combined CH2Cl2 layers are washed with NaHCO3, brine, dried over MgSO4 and concentrated to an oil which is purified by column chromatography eluting with EtOAc/hexane (4:6) to give the desired product as a mixture of two isomers (ratio 2:3).

後処理

  1. extractionthe mixture is extracted three times with CH2Cl2
  2. washThe combined CH2Cl2 layers are washed with NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to an oil which
  5. customis purified by column chromatography
  6. washeluting with EtOAc/hexane (4:6)

出典と根拠

ORDレコード
ord-89872ee1d6be4bb0bfbe4c48058c7d55
出典データセット
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06762198B2

反応ノート

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