Acetic Acid → 1-Biphenyl-2-yl-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Ethyl Ester

HRID 1697618Notes

Reaction equation

HRID 1697618 reaction equation
C=O.[CH2:3]([O:5][C:6](=[O:21])[CH2:7][NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:4].[CH:22]([S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]([F:36])([F:35])[F:34])(=[O:26])=[O:25])=[CH2:23].[C:37](O)(=O)C>C1(C)C=CC=CC=1>[CH2:3]([O:5][C:6]([CH:7]1[CH2:37][CH:22]([S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]([F:34])([F:36])[F:35])(=[O:25])=[O:26])[CH2:23][N:8]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:21])[CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 234667181-Ethenesulfonyl-2-trifluoromethyl-benzeneHCID 28569439Ethyl 2-[(2-phenylphenyl)amino]acetate

Product 1

HCID 667711971-Biphenyl-2-yl-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Ethyl EsterYield 19%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Paraformaldehyde (74 mg, 2.4 mmol) was added to a solution of (biphenyl-2-ylamino)-acetic acid ethyl ester (125 mg, 490 umol; CAS Reg. No. 39950-19-1) in toluene (9 ml) under an argon atmosphere. The mixture was stirred for 1 h at ambient temperature. A solution of 1-ethenesulfonyl-2-trifluoromethyl-benzene (231 mg, 979 umol) in toluene (1 ml) and acetic acid (10 ul, 98 umol) were added and the reaction mixture was heated under reflux conditions to 120° C. for 12 h. The solvent was removed under reduced pressure and purified by column chromatography (silica gel, EtOAc/heptane) to obtain the title compound (47 mg, 93 umol; 19%) as colorless oil. MS (ESI): m/z=504.1 [M+H]+.

Workup

  1. temperaturethe reaction mixture was heated under reflux conditions to 120° C. for 12 h
  2. customThe solvent was removed under reduced pressure
  3. custompurified by column chromatography (silica gel, EtOAc/heptane)

Sources & evidence

ORD record
ord-0051dd1b8b144401a6729984472760c3
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

Loading…