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

HRID 2096239Notes

Reaction equation

HRID 2096239 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].[Cl:24][C:25]1[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][C:26]=1[C:27]([NH:29][CH2:30][C:31](O)=[O:32])=[O:28]>>[C:12]([O:16][C:17]([N:19]1[CH2:22][CH:21]([NH:23][C:31](=[O:32])[CH2:30][NH:29][C:27](=[O:28])[C:26]2[CH:34]=[C:35]([C:38]([F:41])([F:40])[F:39])[CH:36]=[CH:37][C:25]=2[Cl:24])[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 67424872(2-Chloro-5-trifluoromethyl-benzoylamino)-acetic acid

Product 1

HCID 593615793-[2-(2-Chloro-5-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-chloro-5-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-ea96fa46606c4fd4a031c2ca606bec8b
Source dataset
uspto-grants-2013_05
Patent number
US08450304B2

Reaction notes

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