1-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acid → Ethyl 3-(1-{[(tert-butoxy)carbonyl]amino}cyclopropyl)-3-oxopropanoate

HRID 1056104Notes

Reaction equation

HRID 1056104 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(NC1(C(O)=O)CC1)(O[C:21](C)(C)[CH3:22])=O>>[C:1]([O:5][C:6]([NH:8][C:9]1([C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:22][CH2:21]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 6883961-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acidHCID 111285644-((tert-Butoxycarbonyl)amino)-3-oxobutanoic acid ethyl ester

Product 1

HCID 89781999Ethyl 3-(1-{[(tert-butoxy)carbonyl]amino}cyclopropyl)-3-oxopropanoate

Procedure

A tautomeric mixture of ethyl 3-(1-((tert-butoxycarbonyl)amino)cyclopropyl)-3-oxopropanoate and (Z)-ethyl 3-(1-((tert-butoxycarbonyl)amino)cyclopropyl)-3-hydroxyacrylate (3.15 g, 11.61 mmol, 90% yield) as an off white solid was prepared according the procedures described for Intermediate 601, using 1-(Boc-amino)cyclopropanecarboxylic acid (Chem-Impex International, Inc., cat #04052) (2.59 g, 12.87 mmol) as the reagent. m/z (ESI, +ve) 294.2 (M+23)+.

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-334910615d7444ad96af360f66e96e68
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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