Dimethylformamide → HCID 21474814, compound

HRID 1901749Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[O:5][CH2:6][CH:7]([OH:22])[CH2:8][NH:9][C:10]([CH3:21])([CH3:20])[CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].CN(C)[CH:28]=[O:29]>>[Si:13]([O:12][CH2:11][C:10]([N:9]1[CH2:8][CH:7]([CH2:6][O:5][C:4]2[CH:23]=[CH:24][CH:25]=[C:2]([Cl:1])[CH:3]=2)[O:22][C:28]1=[O:29])([CH3:20])[CH3:21])([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:15])[CH3:14]

Participants

Reactant 2

HCID 6228Dimethylformamide

HCID 21474720HCID 21474720, compound

Product 1

HCID 21474814HCID 21474814, compound

Procedure

A procedure similar to that described in Preparation 11 was repeated, except that 5.13 g of 1-(3-chlorophenoxymethyl)-2-(2-t-butyldimethylsilyloxy-1,1-dimethylethylamino)ethanol (prepared as described in Preparation 105), 50 ml of anhydrous dimethylformamide and 2.59 g of N,N'-carbonyldiimidazole were used, to give 5.27 g of the title compound having an Rf value of 0.33 (on silica gel thin layer chromatography, using a 1:4 by volume mixture of ethyl acetate and hexane as the developing solvent).

Workup

customA procedure similar to that described in Preparation 11

Sources & evidence

ORD record: ord-657e63a6779e46ca9e0e490f955a9e7d
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05578620

Reaction notes

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