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

HRID 1884276노트

반응식

HRID 1884276 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 241Benzene용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-41a224d556ea4b4da3e5124b0273696d
출처 데이터셋
uspto-grants-2004_07
특허 번호
US06762198B2

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