Trifluoroacetic acid → 3-(4-Chloro-phenyl)-1-ethyl-1-pyrrolidin-3-yl-urea

HRID 917200Notes

Reaction equation

HRID 917200 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([N:13]([CH2:24][CH3:25])[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[O:15])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:14](=[O:15])[N:13]([CH2:24][CH3:25])[CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66758335HCID 66758335, compound

Product 1

HCID 231369783-(4-Chloro-phenyl)-1-ethyl-1-pyrrolidin-3-yl-urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[3-(4-chloro-phenyl)-1-ethylureido]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.4 g, 1.08 mmol) in dichloromethane (5.0 ml) cooled at 0° C. was treated with trifluoroacetic acid (20%) and warmed to room temperature and stirred for 2 h. The reaction was concentrated in vacuo, diluted with ethyl acetate and free based with 10% aqueous sodium bicarbonate. The combined organics were dried over sodium sulfate. The product was used without any further purification. ESI-MS m/z: 268 (M+1), UV retention time: 1.02 min.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. customThe product was used without any further purification

Sources & evidence

ORD record
ord-4fc730c963804abf857dd9e6821ece3e
Source dataset
uspto-grants-2007_09
Patent number
US07271176B2

Reaction notes

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