Imidazole → HCID 131725363, compound

HRID 891684Notes

Reaction equation

HRID 891684 reaction equation
[C:1]1([P:7]([O:15][C:16]2[C@H:17]([CH3:40])[C@H:18]3[C@@H:35]([C@H:36]([OH:38])[CH3:37])[C:34](=[O:39])[N:19]3[C:20]=2[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=2)=[O:22])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Si:41](Cl)([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42].N1C=CN=C1.CO>CN(C)C=O>[Si:41]([O:38][C@@H:36]([C@H:35]1[C:34](=[O:39])[N:19]2[C:20]([C:21]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([N+:31]([O-:33])=[O:32])=[CH:29][CH:30]=3)=[O:22])=[C:16]([O:15][P:7]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:8])[C@H:17]([CH3:40])[C@@H:18]12)[CH3:37])([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 887MethanolHCID 28928tert-Butyldimethylsilyl chlorideHCID 131720384p-nitrobenzyl (1R,5S,6S)-2-(diphenylphosphoryloxy)-6-[(R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate

Product 1

HCID 131725363HCID 131725363, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of p-nitrobenzyl(1R,5S,6S)-2-(diphenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate (5.00 g, 8.41 mmol) in dimethylformamide (250 ml) were added t-butyldimethylsilyl chloride (2.54 g, 16.8 mmol) and imidazole (1.14 g, 16.8 mmol) in an ice bath, and the reaction mixture was stirred in the ice bath for 7 hours. After checking the completion of the reaction, methanol was added thereto and the resulting mixture was stirred for 30 minutes. The reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution. The obtained organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (3:1) as the eluant to afford p-nitrobenzyl (1R,5S,6S)-6-[(R)-1-t-butyldimethylsilyloxyethyl]-2-(diphenylphosphoryloxy)-1-methylcarbapen-2-em-3-carboxylate (5.27 g, yield 88%) as a pale yellow oil.

Workup

  1. additionwas added
  2. customThe reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution
  3. washThe obtained organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-3f6d95dba7b946ebbe12200aa6c1d7b0
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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