Imidazole → Benzyl N-[2-t-Butyldimethylsilyloxy-1,1-dimethylethyl]carbamate

HRID 1901747Notes

Reaction equation

HRID 1901747 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:16])([CH3:15])[CH2:13][OH:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>CN(C)C=O>[Si:22]([O:14][CH2:13][C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:16])[CH3:15])([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 12325553benzyl N-(1-hydroxy-2-methylpropan-2-yl)carbamate

Product 1

HCID 21474722Benzyl N-[2-t-Butyldimethylsilyloxy-1,1-dimethylethyl]carbamateYield 97.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 8 was repeated, except that 10.00 g of 2-benzyloxycarbonylamino-2-methylpropanol, 7.35 g of imidazole, 150 ml of anhydrous dimethylformamide and 8.14 g of t-butyldimethylsilyl chloride were used, to give 14.68 g of the title compound having an Rf value of 0.73 (on silica gel thin layer chromatography, using a 1:4 by volume mixture of ethyl acetate and hexane as the developing solvent).

Workup

  1. customA procedure similar to that described in Preparation 8

Sources & evidence

ORD record
ord-1e9dd6b2f31b4322a6baafabc16a8550
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

Loading…