1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-[2-(2,5-Bis-trifluoromethyl-benzoylamino)-acetylamino]-azetidine-1-carboxylic acid tert-butylester

HRID 2096236Notes

Reaction equation

HRID 2096236 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]([F:44])([F:43])[C:26]1[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][C:27]=1[C:28]([NH:30][CH2:31][C:32](O)=[O:33])=[O:29]>>[C:12]([O:16][C:17]([N:19]1[CH2:22][CH:21]([NH:23][C:32](=[O:33])[CH2:31][NH:30][C:28](=[O:29])[C:27]2[CH:35]=[C:36]([C:39]([F:42])([F:41])[F:40])[CH:37]=[CH:38][C:26]=2[C:25]([F:24])([F:43])[F:44])[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 86642255(2,5-Bistrifluoromethyl-benzoylamino)-acetic acid

Product 1

HCID 593616073-[2-(2,5-Bis-trifluoromethyl-benzoylamino)-acetylamino]-azetidine-1-carboxylic acid tert-butylester

Procedure

The title compounds were prepared as white solids from EDCI coupling between 3-amino-azetidine-1-carboxylic acid tert-butyl ester and (2,5-bistrifluoromethyl-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-54cb972da51c437da9b9c95c7ee3254a
Source dataset
uspto-grants-2013_05
Patent number
US08450304B2

Reaction notes

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