Dimethylformamide → HCID 21474791, compound

HRID 1901723Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[O:5][CH2:6][CH:7]([OH:21])[CH2:8][NH:9][CH:10]([CH3:20])[CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].CN(C)[CH:27]=[O:28]>>[Si:13]([O:12][CH2:11][CH:10]([N:9]1[CH2:8][CH:7]([CH2:6][O:5][C:4]2[CH:22]=[CH:23][CH:24]=[C:2]([F:1])[CH:3]=2)[O:21][C:27]1=[O:28])[CH3:20])([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:14])[CH3:15]

Participants

Reactant 2

HCID 6228Dimethylformamide

HCID 21474778HCID 21474778, compound

Product 1

HCID 21474791HCID 21474791, compound

Procedure

A procedure similar to that described in Preparation 11 was repeated, except that 2.00 g of 1-(3-fluorophenoxymethyl)-2-(2-t-butyldimethylsilyloxy-1-methylethylamino)ethanol (prepared as described in Preparation 71), 20 ml of anhydrous dimethylformamide and 1.09 g of N,N'-carbonyldiimidazole were used, to give 0.74 g of the title compound having an Rf value of 0.29 (on silica gel thin layer chromatography, using a 1:3 by volume mixture of ethyl acetate and hexane as the developing solvent) from a polar diastereomer and 1.03 g of the title compound, melting at 54° C. to 58° C. from a less polar diastereomer.

Workup

customA procedure similar to that described in Preparation 11

Sources & evidence

ORD record: ord-f8cf4b391ba14addbaf188df285ce380
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05578620

Reaction notes

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