Water → 1-[(2S,3R)-2-benzyloxy-5-(2-oxobenzothiazol-3-yl)-3-pentyl]imidazole-4-carboxamide

HRID 1358498Notes

Reaction equation

[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

Participants

Conditions

Temperature: 65 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-7d5460f6e3734611b331b2cca7655c92
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06596738B1

Reaction notes

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