Methanol → 3-[[N-[3-trifluoromethylbenzoyl]glycyl]aminomethyl]-1-(4-chlorobenzyl)pyrrolidine
Reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[Cl:14][C:15]1[CH:32]=[CH:31][C:18]([CH2:19][N:20]2[CH2:24][CH2:23][CH:22]([CH2:25][NH:26][C:27](=[O:30])[CH2:28][NH2:29])[CH2:21]2)=[CH:17][CH:16]=1.CO>ClCCl.C(Cl)(Cl)Cl>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:29][CH2:28][C:27]([NH:26][CH2:25][CH:22]1[CH2:23][CH2:24][N:20]([CH2:19][C:18]2[CH:31]=[CH:32][C:15]([Cl:14])=[CH:16][CH:17]=2)[CH2:21]1)=[O:30])=[O:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 3-(trifluoromethyl)benzoyl chloride (0.058 mmol) in dichloromethane (0.2 mL) was added to a mixture of 1-(4-chlorobenzyl)-3-{(glycylamino)methyl}pyrrolidine (0.050 mmol) and peperidinomethylpolystyrene (60 mg) in chloroform (0.2 mL) and dichloromethane (1 mL). After the reaction mixture was stirred at room temperature for 2.5 h, methanol (0.30 mL) was added and the mixture was stirred at room temperature for 1 h. The reaction mixture was loaded onto Varian™ SCX column, and washed with CH3OH (15 mL). Product was eluted off using 2 N NH3 in CH3OH (5 mL) and concentrated to afford (3-[{N-(3-trifluoromethylbenzoyl)glycyl}aminomethyl]-1-(4-chlorobenzyl)pyrrolidine (Compound No. 1463) (22.4 mg, 99%): The purity was determined by RPLC/MS (97%); ESIJMS m/e 454.2 (M++H, C22H23ClF3N3O2).
Workup
- stirringthe mixture was stirred at room temperature for 1 h
- washwashed with CH3OH (15 mL)
- washProduct was eluted off
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-21734d6f8337480cae67743698fe521d
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06451842B1
Reaction notes
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