(1R,4S)-4-hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid 2-methyl ester → 5-((1R,2S)-1-tert-Butoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-3-hydroxy-cyclopent-1-enecarboxylic acid methyl ester

HRID 2242418Notes

Reaction equation

HRID 2242418 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C@H:6]([C:11]([OH:13])=O)[CH2:7][C@H:8]([OH:10])[CH:9]=1)=[O:4].[C:14]([O:18][C:19]([C@@:21]1([NH2:26])[CH2:23][C@H:22]1[CH:24]=[CH2:25])=[O:20])([CH3:17])([CH3:16])[CH3:15]>>[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:11](=[O:13])[NH:26][C@:21]2([C:19]([O:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:20])[CH2:23][C@H:22]2[CH:24]=[CH2:25])[CH2:7][CH:8]([OH:10])[CH:9]=1)=[O:4]

Participants

3

Reactant 2

HCID 68410381(1R,4S)-4-hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid 2-methyl esterHCID 68494585(1R,2S)-1-amino-2-vinyl-cyclo-propane carboxylic acid tert-butyl ester

Product 1

HCID 592041965-((1R,2S)-1-tert-Butoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-3-hydroxy-cyclopent-1-enecarboxylic acid methyl ester

Procedure

Reaction of 4 (50 mg, 37 mmol) according to the method described for the preparation of 5 using (1R,2S)-1-amino-2-vinyl-cyclopropane carboxylic acid tert.butyl ester instead of 2-amino-pentanoic acid tert.butyl ester provided the title compound as a slightly yellow oil (50 mg, 38%).

Sources & evidence

ORD record
ord-a2b3fa06d0104465ab7056e56665e903
Source dataset
uspto-grants-2010_03
Patent number
US07671032B2

Reaction notes

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