Water → HCID 57015347, 화합물

HRID 1358498

반응식

HRID 1358498 반응식
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[S:3]1.[H-].[Na+].[CH2:13]([O:20][C@H:21]([C@H:23]([N:31]1[CH:35]=[C:34]([C:36]([NH2:38])=[O:37])[N:33]=[CH:32]1)[CH2:24][CH2:25]OS(C)(=O)=O)[CH3:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C=O)C>[CH2:13]([O:20][C@H:21]([C@H:23]([N:31]1[CH:35]=[C:34]([C:36]([NH2:38])=[O:37])[N:33]=[CH:32]1)[CH2:24][CH2:25][N:6]1[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[S:3][C:2]1=[O:1])[CH3:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 13625BenzothiazoloneHCID 24758Sodium hydrideHCID 11164927HCID 11164927, 화합물

생성물 1

HCID 57015347HCID 57015347, 화합물수율 52.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
65 °C

실험 절차

To a stirred solution of 2-oxobenzothiazole (83 mg, 0.549 mmol) in DMF (3 ml) was added NaH (60% in mineral oil, 22 mg, 0.549 mmol) at room temperature. After 10 minutes, 1-[(2S,3R)-2-benzyloxy-5-methanesulfonyloxy-3-pentyl]imidazole-4-carboxamide in DMF (3 ml) was added and the resulting mixture was stirred for 6 hours at 60 to 70° C. The reaction mixture was poured into water (30 ml) and extracted with ethyl acetate. The organic layer was washed with brine, dried (sodium sulfate), and concentrated in vacuo. The residue was purified by silica gel (8 g) column chromatography eluting with chloroform/methanol (100:1 to 30:1) to give 1-[(2S,3R)-2-benzyloxy-5-(2-oxobenzothiazol-3-yl)-3-pentyl]imidazole-4-carboxamide (63 mg, 52.7%).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel (8 g) column chromatography
  6. washeluting with chloroform/methanol (100:1 to 30:1)

출처 및 근거

ORD 기록
ord-7d5460f6e3734611b331b2cca7655c92
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06596738B1

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