2-Chloropyrimidine → (2S,4R)-1-Pyrimidin-2-yl-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

HRID 1697694Notes

Reaction equation

HRID 1697694 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])(=[O:12])=[O:11])[CH2:7][NH:6]1)=[O:4].C(OC([C@@H]1C[C@H](S(C2C=CC=CC=2C(F)(F)F)(=O)=O)CN1)=O)C.Cl[C:47]1[N:52]=[CH:51][CH:50]=[CH:49][N:48]=1>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:20])[F:21])(=[O:11])=[O:12])[CH2:7][N:6]1[C:47]1[N:52]=[CH:51][CH:50]=[CH:49][N:48]=1)=[O:4]

Participants

4

Reactant 3

HCID 744042-ChloropyrimidineHCID 66770899(2S,4S)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid ethyl esterHCID 66771131(2S,4R)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 66770364(2S,4R)-1-Pyrimidin-2-yl-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Procedure

In analogy to the procedure described in example 335a, (2S,4R)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester (prepared as described for the corresponding (2S,4S)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid ethyl ester in example 192e) was reacted with 2-chloro-pyrimidine (CAS Reg. No. 1722-12-9) in a shaking reactor at 150° C. for 48 h to give the title compound as yellow oil. MS (ESI): m/z=416.1 [M+H]+.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-0c57b44f26e746ae986349a9963ed3fd
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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