(1R,2R,4S)-2-((1R,2S)-1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl) 4-hydroxy-cyclopentanecarboxylic acid tert-butyl ester → 2-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-[2-(3,5-difluoro-phenyl)-7-methoxy-8-methyl-quinazolin-4-yloxy]-cyclopentanecarboxylic acid tert-butyl ester

HRID 1443510Notes

Reaction equation

HRID 1443510 reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][C@@H:11]([OH:13])[CH2:10][C@H:9]1[C:14](=[O:26])[NH:15][C@:16]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:18][C@H:17]1[CH:19]=[CH2:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:27][C:28]1[CH:29]=[C:30]([C:35]2[N:44]=[C:43](O)[C:42]3[C:37](=[C:38]([CH3:48])[C:39]([O:46][CH3:47])=[CH:40][CH:41]=3)[N:36]=2)[CH:31]=[C:32]([F:34])[CH:33]=1>>[C:1]([O:5][C:6]([CH:8]1[CH2:12][CH:11]([O:13][C:43]2[C:42]3[C:37](=[C:38]([CH3:48])[C:39]([O:46][CH3:47])=[CH:40][CH:41]=3)[N:36]=[C:35]([C:30]3[CH:31]=[C:32]([F:34])[CH:33]=[C:28]([F:27])[CH:29]=3)[N:44]=2)[CH2:10][CH:9]1[C:14](=[O:26])[NH:15][C:16]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:18][CH:17]1[CH:19]=[CH2:20])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 59165438(1R,2R,4S)-2-((1R,2S)-1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl) 4-hydroxy-cyclopentanecarboxylic acid tert-butyl esterHCID 178487740HCID 178487740, compound

Product 1

HCID 684095312-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-[2-(3,5-difluoro-phenyl)-7-methoxy-8-methyl-quinazolin-4-yloxy]-cyclopentanecarboxylic acid tert-butyl ester

Procedure

The alcohol 15 and the quinazolinol 128 was reacted according to same procedure described in example 155 which gave the title compound as a white solid slightly contaminated by triphenyl phosphine oxide (1.245 g, >100%), LRMS (M+H) 652.

Sources & evidence

ORD record
ord-e389c77ccedd497abe015726fccf3a49
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

Loading…