Imidazole → HCID 19099269, compound

HRID 1975480Notes

Reaction equation

HRID 1975480 reaction equation
[CH2:1]([O:4][C:5]([NH:7][CH2:8][CH:9]([CH2:13][NH:14][C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16])[CH:10]([OH:12])[CH3:11])=[O:6])[CH:2]=[CH2:3].N1C=CN=C1.[Si:26](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>CN(C)C=O.C(OCC)(=O)C>[CH2:18]([O:17][C:15]([NH:14][CH2:13][CH:9]([CH2:8][NH:7][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[CH:10]([O:12][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[CH3:11])=[O:16])[CH:19]=[CH2:20]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 190993021-allyloxycarbonylamino-2-(N-allyloxycarbonylaminomethyl)butan-3-ol

Product 1

HCID 19099269HCID 19099269, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-allyloxycarbonylamino-2-(N-allyloxycarbonylaminomethyl)butan-3-ol (90.00 g) in N,N-dimethylformamide (800 ml) were added imidazole (85.51 g) and t-butyldimethylsilyl chloride (61.53 g). The resulting mixture was allowed to stand at ambient temperature for 14 hours. The mixture was diluted with ethyl acetate (2.4 l), washed successively with water (1.6 l) and brine (1 l), and dried over magnesium sulfate. Removal of the solvents gave a residue, which was chromatographed on silica gel (1 l) eluting with a mixture of n-hexane and ethyl acetate (9:1-7:3, V/V) to give 1-allyloxycarbonylamino-2-(N-allyloxycarbonylaminomethyl)-3-(t-butyldimethylsilyloxy)butane (115.40 g).

Workup

  1. washwashed successively with water (1.6 l) and brine (1 l)
  2. dry with materialdried over magnesium sulfate
  3. customRemoval of the solvents
  4. customgave a residue, which
  5. customwas chromatographed on silica gel (1 l)
  6. washeluting with a mixture of n-hexane and ethyl acetate (9:1-7:3, V/V)

Sources & evidence

ORD record
ord-e275b51600f24c4c8c776e65f7e02f85
Source dataset
uspto-grants-1994_02
Patent number
US05286721

Reaction notes

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