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Benzyl mercaptan → 3-[(4'-Methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-2-oxo-5-[(benzylthio)methyl]-tetrahydrofuran

HRID 413368
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HRID 413368 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH:19]([CH2:24][CH:25]3[O:27][CH2:26]3)[C:20](OC)=[O:21])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C([O-])(O)=O.[Na+].CCN(CC)CC.[CH2:40]([SH:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[CH:11][C:12]([S:15]([NH:18][CH:19]3[CH2:24][CH:25]([CH2:26][S:47][CH2:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[O:27][C:20]3=[O:21])(=[O:17])=[O:16])=[CH:13][CH:14]=2)=[CH:7][CH:8]=1
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7

반응물 4

HCID 7509Benzyl mercaptanHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 12073922Methyl 2-[(4'-methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-4,5-epoxypentanoate

생성물 1

HCID 235082703-[(4'-Methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-2-oxo-5-[(benzylthio)methyl]-tetrahydrofuran

시약·촉매·용매 2

HCID 241
Benzene
용매
HCID 962Water용매

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온도
70 °C

실험 절차

To a solution of methyl 2-[(4′-methoxy[1,1′-biphenyl]-4-yl)sulfonyl]amino-4,5-epoxypentanoate 1d (0.5 g, 1.28 mmol) in benzene (3 mL), NaHCO3 (0.32 g, 3.84 mmol) and Et3N (0.23 mL, 1.6 mmol) at room temperature is added slowly benzyl mercaptan (0.62 mL, 4.99 mmol). The reaction mixture is heated at 70° C. for 3 h, and stirred two days at room temperature. 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 hexane/EtOAc (4:1) to give the desired product.

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 hexane/EtOAc (4:1)

출처 및 근거

ORD 기록
ord-58e6714a78dc4ad880b5621a36a87da4
출처 데이터셋
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06566381B1

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