Trifluoroacetic acid methylene chloride → HCID 59249253, compound

HRID 1807151Notes

Reaction equation

HRID 1807151 reaction equation
C([O:5][C:6](=[O:44])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([C@H:16]2[C@H:20]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=3[F:28])[C@:19]([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=3[F:38])([C:29]#[N:30])[C@H:18]([CH2:39][C:40]([CH3:43])([CH3:42])[CH3:41])[NH:17]2)=[O:15])[CH:8]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>CO>[Cl:27][C:23]1[C:22]([F:28])=[C:21]([C@@H:20]2[C@:19]([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=3[F:38])([C:29]#[N:30])[C@H:18]([CH2:39][C:40]([CH3:43])([CH3:41])[CH3:42])[NH:17][C@H:16]2[C:14]([NH:13][C:9]2[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=2)[C:6]([OH:44])=[O:5])=[O:15])[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 59249472HCID 59249472, compound

Product 1

HCID 59249253HCID 59249253, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

rac 3-{[(2R,3S,4R,5S)-3-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carbonyl]-amino}-benzoic acid t-butyl ester (26 mg, 0.411 mmol) was treated with 50% TFA/methylene chloride (10 mL) overnight. Removal of solvent and freeze drying of the residue give a white powder. 250 mg. The solid was resolved on a Berger SFC system on a Whelk column under 100 bar, 30° C., and 45% of methanol to give two peaks: Peak 1, undesired enantiomer, 78 mg; Peak 2, 77 mg as white solid.

Workup

  1. customRemoval of solvent and freeze
  2. customdrying of the residue
  3. customgive a white powder
  4. customto give two peaks

Sources & evidence

ORD record
ord-db64b52995254e32959b383accdf554b
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

Loading…