Dichloro-1,2,4-thiadiazole → (2S,4R)-1-(3-Chloro-[1,2,4]thiadiazol-5-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

HRID 1697689Notes

Reaction equation

HRID 1697689 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:46][C:47]1[N:51]=[C:50](Cl)[S: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:50]1[S:49][N:48]=[C:47]([Cl:46])[N:51]=1)=[O:4]

Participants

4

Reactant 3

HCID 2725055Dichloro-1,2,4-thiadiazoleHCID 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 66772233(2S,4R)-1-(3-Chloro-[1,2,4]thiadiazol-5-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 3,5-dichloro-[1,2,4]thiadiazole (CAS Reg. No. 2254-88-8) in a shaking reactor at 55° C. for 12 h to give the title compound as orange solid. MS (ESI): m/z=456.2 [M+H]+.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-e47da782b7ed46788ed65a044f0f1e9c
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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