(2S,4S)-4-Acetylthio-1-allyloxycarbonyl-2-carboxypyrrolidine → (3S,5S)-3-Acetylthio-1-allyloxycarbonyl-5-[N-(imidazo[5,1-b]thiazol-5-yl)methyl-N-methylaminocarbonyl]pyrrolidine

HRID 568260Notes

Reaction equation

HRID 568260 reaction equation
[C:1]([S:4][C@H:5]1[CH2:9][C@@H:8]([C:10]([OH:12])=O)[N:7]([C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])[CH2:6]1)(=[O:3])[CH3:2].C[N+](C)=CCl.[Cl-].ClCCl.[CH3:28][NH:29][CH2:30][C:31]1[N:38]2[C:34]([S:35][CH:36]=[CH:37]2)=[CH:33][N:32]=1>>[C:1]([S:4][C@H:5]1[CH2:9][C@@H:8]([C:10]([N:29]([CH2:30][C:31]2[N:38]3[C:34]([S:35][CH:36]=[CH:37]3)=[CH:33][N:32]=2)[CH3:28])=[O:12])[N:7]([C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 15299255(2S,4S)-4-Acetylthio-1-allyloxycarbonyl-2-carboxypyrrolidineHCID 212624035-(N-Methylamino)methylimidazo[5,1-b]thiazoleHCID 131722372Vilsmeier reagent dichloromethane

Product 1

HCID 20639589(3S,5S)-3-Acetylthio-1-allyloxycarbonyl-5-[N-(imidazo[5,1-b]thiazol-5-yl)methyl-N-methylaminocarbonyl]pyrrolidineYield 47.4%

Procedure

The procedure of Synthesis Example 1 is repeated, except that 260 mg of (3S,5S)-3-acetylthio-1-allyloxycarbonylpyrrolidin-5-carboxylic acid, 0.95 ml of a 1.1 M Vilsmeier reagent/dichloromethane solution, and 159 mg of 5-(N-methylaminomethyl)imidazo[5,1-b]thiazole. Thus, 190.6 mg of the title compound is prepared as a slightly yellow amorphous material.

Workup

  1. customThe procedure of Synthesis Example 1

Sources & evidence

ORD record
ord-2edad9807fc045e4b42036d5bc28a85a
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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