Water → HCID 69527038, compound

HRID 1829813Notes

Reaction equation

HRID 1829813 reaction equation
[Si:1]([O:8][C@H:9]([C@H:11]([N:19]1[CH:23]=[C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:21]=[CH:20]1)[CH2:12][CH2:13]OS(C)(=O)=O)[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][C:30]=1[SH:39].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Si:1]([O:8][C@H:9]([C@H:11]([N:19]1[CH:23]=[C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:21]=[CH:20]1)[CH2:12][CH2:13][S:39][C:30]1[CH:31]=[CH:32][C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:29]=1)[CH3:10])([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 70582-NaphthalenethiolHCID 11430Potassium CarbonateHCID 86595160HCID 86595160, compound

Product 1

HCID 69527038HCID 69527038, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of ethyl 1-[(2S,3R)-2-(tert-butyldimethylsilyloxy)-5-methanesulfonyloxy-3-pentyl]imidazole-4-carboxylate (160 mg, 0.368 mmol) and 2-naphthalenethiol (118 mg, 0.736 mmol) in DMF (5 ml) was added potassium carbonate (102 mg, 0.736 mmol) at room temperature and the reaction mixture was stirred for 2 hours. The resulting reaction mixture was poured into water (25 ml) and extracted with ethyl acetate. The organic layer was washed with brine, dried (sodium sulfate) and evaporated in vacuo. The residue was purified by silica gel (10 g) chromatography eluting with chloroform/methanol (100:1 to 50:1) to give ethyl 1-[(2S,3R)-2-(tert-butyldimethylsilyloxy)-5-(2-naphthylthio)-3-pentyl]imidazole-4-carboxylate (146 mg, 79.5%).

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (sodium sulfate)
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel (10 g) chromatography
  7. washeluting with chloroform/methanol (100:1 to 50:1)

Sources & evidence

ORD record
ord-630f408317a24463949d5f8947d88212
Source dataset
uspto-grants-2006_06
Patent number
US07064144B2

Reaction notes

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