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Benzyl mercaptan → 2-[(4'-Methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-4-hydroxy-5-(benzylthio)-pentanoic Acid

HRID 1884281
ノート
印刷プレビュー

反応式

HRID 1884281 の反応式
[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]3[CH2:23][CH:22]([CH2:24][S:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[O:21][C:20]3=[O:33])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C[O:35]C1C=CC(C2C=CC(S(NC(CC3OC3)C(OC)=O)(=O)=O)=CC=2)=CC=1.C([O-])(O)=O.[Na+].CCN(CC)CC.C(S)C1C=CC=CC=1>C1C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([S:15]([NH:18][CH:19]([CH2:23][CH:22]([OH:35])[CH2:24][S:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:20]([OH:21])=[O:33])(=[O:17])=[O:16])=[CH:13][CH:14]=2)=[CH:5][CH:4]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 7509Benzyl mercaptanHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 12073922Methyl 2-[(4'-methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-4,5-epoxypentanoateHCID 235082703-[(4'-Methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-2-oxo-5-[(benzylthio)methyl]-tetrahydrofuran

生成物 1

HCID 9935779
2-[(4'-Methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-4-hydroxy-5-(benzylthio)-pentanoic Acid

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

3-[(4′-Methoxy[1,1′-biphenyl]-4-yl)sulfonyl]amino-2-oxo-5-[(benzylthio)methyl]-tetrahydrofuran: 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.

後処理

  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)

出典と根拠

ORDレコード
ord-2fe273520e614b94922213c95c08d74f
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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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート