Ammonia → HCID 69527452, compound

HRID 1829805Notes

Reaction equation

HRID 1829805 reaction equation
[Si:1]([O:8][C@H:9]([C@H:11]([N:15]1[CH:19]=[C:18]([C:20]([O:22]CC)=O)[N:17]=[CH:16]1)[CH2:12][CH2:13][OH:14])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH3:25]>CO>[Si:1]([O:8][C@H:9]([C@H:11]([N:15]1[CH:19]=[C:18]([C:20]([NH2:25])=[O:22])[N:17]=[CH:16]1)[CH2:12][CH2:13][OH:14])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 69527792HCID 69527792, compound

Product 1

HCID 69527452HCID 69527452, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 1-[(2S,3R)-2-(tert-butyldimethylsilyloxy)-5-hydroxy-3-pentyl]imidazole-4-carboxylate (1.0 g, 2.8 mmol) in methanol (15 ml) was added aqueous 28% NH3 solution (15 ml). And the mixture was heated at 100° C. in a sealed steel tube for 15 h. After cooling, the reaction mixture was concentrated in vacuo. The residue was purified by silica gel (35 g) chromatography eluting with chloroform/methanol (25:1 to 15:1) to give 1-[(2S,3R)-2-(tert-butyldimethylsilyloxy)-5-hydroxy-3-pentyl]imidazole-4-carboxamide (769.5 mg, 83.8%) as a white amorphous solid.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe residue was purified by silica gel (35 g) chromatography
  4. washeluting with chloroform/methanol (25:1 to 15:1)

Sources & evidence

ORD record
ord-d5b90b982583449683d6b924e80d483c
Source dataset
uspto-grants-2006_06
Patent number
US07064144B2

Reaction notes

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