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

HRID 1443455Notes

Reaction equation

HRID 1443455 reaction equation
[CH3:1][O:2][C:3]1[C:12]([CH3:13])=[C:11]2[C:6]([C:7]([OH:20])=[N:8][C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:10]2)=[CH:5][CH:4]=1.[C:21]([O:25][C:26]([C@@H:28]1[CH2:32][C@@H:31](O)[CH2:30][C@H:29]1[C:34](=[O:46])[NH:35][C@:36]1([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:38][C@H:37]1[CH:39]=[CH2:40])=[O:27])([CH3:24])([CH3:23])[CH3:22]>>[C:21]([O:25][C:26]([CH:28]1[CH2:32][CH:31]([O:20][C:7]2[C:6]3[C:11](=[C:12]([CH3:13])[C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:10]=[C:9]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:8]=2)[CH2:30][CH:29]1[C:34](=[O:46])[NH:35][C:36]1([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:38][CH:37]1[CH:39]=[CH2:40])=[O:27])([CH3:24])([CH3:22])[CH3:23]

Participants

3

Reactant 2

HCID 59165438(1R,2R,4S)-2-((1R,2S)-1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl) 4-hydroxy-cyclopentanecarboxylic acid tert-butyl esterHCID 178487728HCID 178487728, compound

Product 1

HCID 684094132-(1-Ethoxycarbonyl-2-vinylcyclopropylcarbamoyl)-4-(7-methoxy-8-methyl-2-phenyl-quinazolin-4-yloxy)-cyclopentanecarboxylic acid tert-butyl esterYield 75.8%

Procedure

Quinazolinol derivative (83) (480 mg, 1.8 mmol) was coupled to compound 15 (0.55 mg, 1.5 mmol) as described in example 16, which gave the title compound (700 mg, 75%)

Sources & evidence

ORD record
ord-612d3c31a1464540b23df7105cb57bd8
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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