Ammonia → (RS)-2-Oxo-1-[4-(4-trifluoromethyl-benzyloxy)-phenyl]-pyrrolidine-3-carboxylic Acid Amide

HRID 1768143Notes

Reaction equation

HRID 1768143 reaction equation
[O:1]=[C:2]1[CH:6]([C:7](O)=[O:8])[CH2:5][CH2:4][N:3]1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)=[CH:12][CH:11]=1.O[N:29]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.N>C1COCC1>[O:1]=[C:2]1[CH:6]([C:7]([NH2:29])=[O:8])[CH2:5][CH2:4][N:3]1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23614753(RS)-2-oxo-1-[4-(4-trifluoromethyl-benzyloxy)-phenyl]-pyrrolidine-3-carboxylic acid

Product 1

HCID 10429719(RS)-2-Oxo-1-[4-(4-trifluoromethyl-benzyloxy)-phenyl]-pyrrolidine-3-carboxylic Acid AmideYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

150 mg (0.4 mmol) (RS)-2-oxo-1-[4-(4-trifluoromethyl-benzyloxy)-phenyl]-pyrrolidine-3-carboxylic acid is dissolved in 4 ml THF. 59 mg (0.43 mmol) of 1-hydroxybenzotriazole and 80 mg (0.42 mmol) of N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide-hydrochloride is added and the reaction mixture is stirred at RT for 30 min. After cooling to 0° C. 4 ml of concentrated ammonia is added and the resulting mixture stirred at RT for 1 hour. Dilution with water, extraction and chromatography (silica gel, ethyl acetate) yields 15 mg (10%) of a colorless solid. MS: m/e=379.2 (M+H)+.

Workup

  1. temperatureAfter cooling to 0° C
  2. stirringthe resulting mixture stirred at RT for 1 hour
  3. extractionDilution with water, extraction and chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-dd1b64e1d194467282ecc6192ee37dda
Source dataset
uspto-grants-2007_06
Patent number
US07235581B2

Reaction notes

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