Water → HCID 69677845, compound

HRID 1072055Notes

Reaction equation

HRID 1072055 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([NH2:8])=[O:7])[N:3]=[CH:2]1.[H-].[Na+].[CH2:11]([O:18][C@@H:19]([CH3:36])[C@@H:20](OS(C)(=O)=O)[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29][CH3:30])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>CN(C=O)C>[CH2:11]([O:18][C@H:19]([C@H:20]([N:1]1[CH:5]=[C:4]([C:6]([NH2:8])=[O:7])[N:3]=[CH:2]1)[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29][CH3:30])[CH3:36])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 152917Imidazole-4-carboxamideHCID 86592320HCID 86592320, compound

Product 1

HCID 69677845HCID 69677845, compoundYield 11.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of imidazole-4-carboxamide (313 mg) in DMF (3.8 ml) was treated with sodium hydride (60% in mineral oil, 129 mg) at ice-bath temperature and the mixture was stirred at room temperature for 20 min. A solution of 2-[(3S,4S)-4-benzyloxy-3-methanesulfonyloxypentyl]thioanisole (0.92 g) in DMF (7.5 ml) was added and the mixture was stirred at 85° C. for 3 days. The mixture was poured into water and extracted with ethyl acetate. The extract was washed with water, dried and concentrated in vacuo. Column chromatography (dichloromethane:methanol=30:1) gave 1-[(2S,3R)-2-benzyloxy-5-(2-(methylthio)phenyl)-3-pentyl]imidazole-4-carboxamide (1) (96.4 mg, 11.6%) as a pale yellow oil.

Workup

  1. stirringthe mixture was stirred at 85° C. for 3 days
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e6473427691b428188c381a453b5ac54
Source dataset
uspto-grants-2005_06
Patent number
US06908940B2

Reaction notes

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