Tetrahydrofuran → 2-[(4'-Methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-4-hydroxy-5-[(2-thiazolyl)thio]-pentanoic Acid

HRID 1884276ノート

反応式

HRID 1884276 の反応式
O1CCCC1.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH:23][CH:24]([CH2:29][CH:30]3[O:32][CH2:31]3)[C:25]([O:27]C)=[O:26])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.CCN(CC)CC.[SH:40][C:41]1[S:42][CH:43]=[CH:44][N:45]=1>C1C=CC=CC=1.O>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]([S:20]([NH:23][CH:24]([CH2:29][CH:30]([OH:32])[CH2:31][S:40][C:41]3[S:42][CH:43]=[CH:44][N:45]=3)[C:25]([OH:27])=[O:26])(=[O:22])=[O:21])=[CH:18][CH:19]=2)=[CH:10][CH:9]=1

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 12073922Methyl 2-[(4'-methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-4,5-epoxypentanoateHCID 178527881HCID 178527881、化合物

生成物 1

HCID 98919232-[(4'-Methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-4-hydroxy-5-[(2-thiazolyl)thio]-pentanoic Acid

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 962Water溶媒

実験手順

3-[(4′-Methoxy[1,1′-biphenyl]-4-yl)sulfonyl]amino-[2-oxo-5-(thiazol-2-yl)thio]methyl]-tetrahydrofuran: To a solution of methyl 2-[(4′-methoxy[1,1′-biphenyl]-4-yl)sulfonyl]amino-4,5-epoxypentanoate 1d (0.7 g, 1.79 mmol) in benzene (5 mL) and Et3N (0.33 mL, 2.3 mmol) at room temperature is added slowly 2-mercaptothiazole (0.52 g, 4.48 mmol). The reaction mixture is stirred for 4 h at room temperature. The resulting mixture is diluted with water, and the mixture is then extracted three times with EtOAc. The combined EtOAc layer is consecutively washed with water, and brine, dried over MgSO4 and concentrated to an oil under reduced pressure. Purification is accomplished by column chromatography with hexane/EtOAc (4:1 to 7:3 to 6:4) eluent to give the desired product.

後処理

  1. extractionthe mixture is then extracted three times with EtOAc
  2. washThe combined EtOAc layer is consecutively washed with water, and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to an oil under reduced pressure
  5. customPurification

出典と根拠

ORDレコード
ord-41a224d556ea4b4da3e5124b0273696d
出典データセット
uspto-grants-2004_07
特許番号
US06762198B2

反応ノート

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