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

HRID 1884279
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HRID 1884279 반응식
[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
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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

생성물 1

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

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
HCID 516892Sodium Bicarbonate용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-89872ee1d6be4bb0bfbe4c48058c7d55
출처 데이터셋
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06762198B2

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