1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-[2-(3-Trifluoromethyl-5-fluoro-benzoylamino)-acetylamino]-azetidine-1-carboxylic acid tert-butyl ester

HRID 2096229Notes

Reaction equation

HRID 2096229 reaction equation
CCN=C=NCCCN(C)C.[C:12]([O:16][C:17]([N:19]1[CH2:22][CH:21]([NH2:23])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[F:24][C:25]1[CH:26]=[C:27]([C:38]([F:41])([F:40])[F:39])[CH:28]=[C:29]([CH:37]=1)[C:30]([NH:32][CH2:33][C:34](O)=[O:35])=[O:31]>>[C:12]([O:16][C:17]([N:19]1[CH2:22][CH:21]([NH:23][C:34](=[O:35])[CH2:33][NH:32][C:30](=[O:31])[C:29]2[CH:37]=[C:25]([F:24])[CH:26]=[C:27]([C:38]([F:39])([F:41])[F:40])[CH:28]=2)[CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

4

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 66744533(5-Fluoro-3-trifluoromethyl-benzoylamino)-acetic acid

Product 1

HCID 593615843-[2-(3-Trifluoromethyl-5-fluoro-benzoylamino)-acetylamino]-azetidine-1-carboxylic acid tert-butyl ester

Procedure

The title compounds were prepared as white solids from EDCI coupling between 3-amino-azetidine-1-carboxylic acid tert-butyl ester (AstaTech) and (5-fluoro-3-trifluoromethyl-benzoylamino)-acetic acid (prepared by the method similar to Ingersoll, A. W. et. al., Organic Syntheses 1932, XII, 40-2) using the procedure described in Step C of Example 1.

Workup

  1. customprepared by the method similar to Ingersoll

Sources & evidence

ORD record
ord-c0f854f10e124642bd15caf26d549ad1
Source dataset
uspto-grants-2013_05
Patent number
US08450304B2

Reaction notes

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