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

HRID 1697679Notes

Reaction equation

HRID 1697679 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[Cl:19])(=[O:12])=[O:11])[CH2:7][NH:6]1)=[O:4].Cl[C:21]1[S:22][C:23]([C:26]([F:29])([F:28])[F:27])=[N:24][N:25]=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[Cl:19])(=[O:11])=[O:12])[CH2:7][N:6]1[C:21]1[S:22][C:23]([C:26]([F:29])([F:28])[F:27])=[N:24][N:25]=1)=[O:4]

Participants

3

Reactant 2

HCID 132467892-Chloro-5-trifluoromethyl-(1,3,4)thiadiazoleHCID 66770749(2S,4R)-methyl 4-(2-chlorophenylsulfonyl)pyrrolidine-2-carboxylate

Product 1

HCID 66772319(2S,4R)-4-(2-Chloro-benzenesulfonyl)-1-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Procedure

In analogy to the procedure described in example 335a, (2S,4R)-4-(2-chloro-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester (example 253a) was reacted with 2-chloro-5-trifluoromethyl-[1,3,4]thiadiazole (CAS Reg. No. 53645-98-0) in a shaking reactor at 55° C. for 12 h to give the title compound as orange oil. MS (ESI): m/z=456.0 [M+H]

Sources & evidence

ORD record
ord-f5b9b16a51a842928530e09aae73b0ac
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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