Imidazole → Ethyl 2-azido-3-t-butyldimethylsilyloxy-3-(2-chloropyridin-3-yl)propionate

HRID 55521Notes

Reaction equation

HRID 55521 reaction equation
[N:1]([CH:4]([CH:10]([C:12]1[C:13]([Cl:18])=[N:14][CH:15]=[CH:16][CH:17]=1)[OH:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3].[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].N1C=CN=C1>CN(C)C=O>[N:1]([CH:4]([CH:10]([O:11][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[C:12]1[C:13]([Cl:18])=[N:14][CH:15]=[CH:16][CH:17]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 23298278Ethyl 2-azido-3-(2-chloropyridin-3-yl)-3-hydroxypropionate

Product 1

HCID 23298343Ethyl 2-azido-3-t-butyldimethylsilyloxy-3-(2-chloropyridin-3-yl)propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 49 was repeated, except that 3.90 g of ethyl 2-azido-3-(2-chloropyridin-3-yl)-3-hydroxypropionate (prepared as described in Preparation 76), 8.6 g of t-butyldimethylsilyl chloride, 10 g of imidazole and 80 ml of dimethylformamide were used, to give the title compound as a crude product. This crude product was purified by column chromatography through silica gel, using a 8:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 5.6 g of the title compound having Rf=0.31 (on silica gel thin layer chromatography using a 3:1 by volume mixture of hexane and ethyl acetate as the developing solvent).

Workup

  1. customA procedure similar to that described in Preparation 49

Sources & evidence

ORD record
ord-4b644a5b810644e495d73e66c6c4febf
Source dataset
uspto-grants-1997_04
Patent number
US05624935

Reaction notes

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