Methanesulfonyl chloride → 3-{(3S,5R)-1-[4-(4-chlorophenoxy)phenyl]-5-[3-(trifluoromethyl)phenyl]-2-oxopyrrolidin-3-yl}propyl methanesulfonate

HRID 1972252Notes

Reaction equation

HRID 1972252 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=4)[CH2:16][C@H:15]([CH2:28][CH2:29][CH2:30][OH:31])[C:14]3=[O:32])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>C(Cl)Cl>[CH3:35][S:36]([O:31][CH2:30][CH2:29][CH2:28][C@H:15]1[CH2:16][C@H:17]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:27])[F:25])[CH:19]=2)[N:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:34][CH:33]=3)=[CH:12][CH:11]=2)[C:14]1=[O:32])(=[O:38])=[O:37]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 59485594(3S,5R)-1-[4-(4-chlorophenoxy)phenyl]-5-[3-(trifluoromethyl)phenyl]-3-(3-hydroxypropyl)pyrrolidin-2-one

Product 1

HCID 594860113-{(3S,5R)-1-[4-(4-chlorophenoxy)phenyl]-5-[3-(trifluoromethyl)phenyl]-2-oxopyrrolidin-3-yl}propyl methanesulfonateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S,5R)-1-[4-(4-chlorophenoxy)phenyl]-5-[3-(trifluoromethyl)phenyl]-3-(3-hydroxypropyl)pyrrolidin-2-one (34 mg, 0.070 mmol) in DCM (3 mL) at 0° C. is added MsCl (50 μL) and TEA (100 μL). The reaction mixture is stirred at room temperature overnight before removal of the solvent. The residue is purified on silica gel (0-50% ethyl acetate in hexane) to give 3-{(3S,5R)-1-[4-(4-chlorophenoxy)phenyl]-5-[3-(trifluoromethyl)phenyl]-2-oxopyrrolidin-3-yl}propyl methanesulfonate (39.1 mg, 99%) as a colorless oil.

Workup

  1. customThe residue is purified on silica gel (0-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-39319d27dfc242928bc0ba8c30da7325
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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