1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-[2-(4-Fluoro-3-trifluoromethyl-benzoylamino)-acetylamino]-azetidine-1-carboxylic acid tert-butylester

HRID 1893308Notes

Reaction equation

HRID 1893308 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:37]=[CH:36][C:28]([C:29]([NH:31][CH2:32][C:33](O)=[O:34])=[O:30])=[CH:27][C:26]=1[C:38]([F:41])([F:40])[F:39]>>[C:12]([O:16][C:17]([N:19]1[CH2:22][CH:21]([NH:23][C:33](=[O:34])[CH2:32][NH:31][C:29](=[O:30])[C:28]2[CH:36]=[CH:37][C:25]([F:24])=[C:26]([C:38]([F:39])([F:41])[F:40])[CH:27]=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 61709338(4-Fluoro-3-trifluoromethyl-benzoylamino)-acetic acid

Product 1

HCID 595419223-[2-(4-Fluoro-3-trifluoromethyl-benzoylamino)-acetylamino]-azetidine-1-carboxylic acid tert-butylester

Procedure

The title compounds were prepared as white solids from the EDCI coupling of 3-amino-azetidine-1-carboxylic acid tert-butyl ester (BetaPharma) and (4-fluoro-3-trifluoromethyl-benzoylamino)-acetic acid (analog synthesis by the procedure described in Organic Synthesis XII, 40-2, 1932) using the procedure described in Step F of Example 1.

Workup

  1. customanalog synthesis by the procedure

Sources & evidence

ORD record
ord-329442d9aa2c4386b496d9a1d836b856
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

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