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

HRID 1884280
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HRID 1884280 반응식
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([S:7]([NH:10][CH:11]2[CH2:15][CH:14]([CH2:16][S:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:13][C:12]2=[O:24])(=[O:9])=[O:8])=[CH:3][CH:2]=1.C1(C2C=CC=CC=2)C=CC(S(NC(CC2OC2)C(OC)=O)(=O)=[O:38])=CC=1.CCN(CC)CC.C1(S)C=CC=CC=1>C1C=CC=CC=1.O>[C:1]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:6]=[CH:5][C:4]([S:7]([NH:10][CH:11]([CH2:15][CH:14]([OH:38])[CH2:16][S:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]([OH:13])=[O:24])(=[O:8])=[O:9])=[CH:3][CH:2]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 7969ThiophenolHCID 8471TriethylamineHCID 23508251Methyl 2-[[(1,1'-biphenyl)-4-yl]sulfonyl]amino-4,5-epoxypentanoateHCID 235082763-[[(1,1'-Biphenyl)-4-yl]sulfonyl]amino-2-oxo-5-[(phenylthio)methyl]-tetrahydrofuran

생성물 1

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

시약·촉매·용매 2

HCID 241Benzene용매HCID 962Water용매

실험 절차

3-[[(1,1′-Biphenyl)-4-yl]sulfonyl]amino-2-oxo-5-[(phenylthio)methyl]-tetrahydrofuran: To a solution of methyl 2-[[(1,1′-biphenyl)-4-yl]sulfonyl]amino-4,5-epoxypentanoate 16b (0.36 g, 1.47 mmol) in benzene (5 mL) and Et3N (0.27 g, 1.91 mmol) at room temperature is added slowly benzenethiol (0.38 mL, 3.67 mmol). The reaction mixture is stirred for 3 hrs. The resulting mixture is diluted with water, and then the mixture is extracted three times with EtOAc. The combined EtOAc layer is washed with water, brine, dried over MgSO4 and concentrated to an oil which is purified by column chromatography eluting with EtOAc/hexane (1:4 to 3:7) to give the desired product as a mixture of two isomers (ratio: ˜2:1).

후처리

  1. extractionthe mixture is extracted three times with EtOAc
  2. washThe combined EtOAc layer is washed with water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to an oil which
  5. customis purified by column chromatography
  6. washeluting with EtOAc/hexane (1:4 to 3:7)

출처 및 근거

ORD 기록
ord-e87615f3711d4298b5f6dcb4749711f5
출처 데이터셋
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06762198B2

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