Imidazole → HCID 57019258, compound

HRID 1976230Notes

Reaction equation

HRID 1976230 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@@H:4]1[CH2:8][C@@H:7]([OH:9])[CH2:6][N:5]1[C:10](=[O:20])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].N1C=CN=C1.[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:21])[C@@H:4]1[CH2:8][C@@H:7]([O:9][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH2:6][N:5]1[C:10](=[O:20])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 11415164HCID 11415164, compound

Product 1

HCID 57019258HCID 57019258, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 10.7 g of (2S, 4R)-4-hydroxy-1-(2-nitrobenzoyl) proline methyl ester and 5.7 g of imidazole in 100 ml of N,N-dimethylformamide, there was added 6.6 g of tert-butyldimethylsilyl chloride at room temperature in a nitrogen gas atmosphere and the mixture was stirred at room temperature for 2.5 hours. The reaction solution was poured into ice water, followed by extraction with ethyl acetate three times, water washing of the organic phase, drying and concentration thereof under reduced pressure. The resulting residue was subjected to silica gel column chromatography, then eluted with a 1/1 ethyl acetate/hexane mixed solvent, followed by recrystallization from ethyl acetate-hexane to give 10.6 g (yield 71.6%) of (2S, 4R)-4-(tert-butyldimethylsilyloxy)-1-(2-nitrobenzoyl) proline methyl ester as colorless needles.

Workup

  1. extractionfollowed by extraction with ethyl acetate three times, water
  2. washwashing of the organic phase
  3. customdrying
  4. concentrationconcentration
  5. washeluted with a 1/1 ethyl acetate/hexane mixed solvent
  6. customfollowed by recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-7e5c813f1e92451d89f1da6da6f400b4
Source dataset
uspto-grants-2001_05
Patent number
US06225306B1

Reaction notes

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