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

HRID 568261Notes

Reaction equation

HRID 568261 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.[CH2:28]([O:31][C:32]([NH:34][CH2:35][C:36]1[N:43]2[C:39]([S:40][CH:41]=[C:42]2[CH2:44][NH:45][CH3:46])=[CH:38][N:37]=1)=[O:33])[CH:29]=[CH2:30]>C(N(CC)CC)C>[C:1]([S:4][C@H:5]1[CH2:9][C@@H:8]([C:10]([N:45]([CH2:44][C:42]2[N:43]3[C:36]([CH2:35][NH:34][C:32]([O:31][CH2:28][CH:29]=[CH2:30])=[O:33])=[N:37][CH:38]=[C:39]3[S:40][CH:41]=2)[CH3:46])=[O:12])[N:7]([C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 15299255(2S,4S)-4-Acetylthio-1-allyloxycarbonyl-2-carboxypyrrolidineHCID 212623905-allyloxycarbonylaminomethyl-3-(N-methylamino-methyl)imidazo[5,1-b]thiazoleHCID 131722372Vilsmeier reagent dichloromethane

Product 1

HCID 20639588(3S,5S)-3-Acetylthio-1-allyloxycarbonyl-5-[N-[5-(allyloxycarbonylaminomethyl)imidazo[5,1-b]thiazol-3-yl]methyl-N-methylaminocarbonyl]pyrrolidineYield 65.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The procedure of Synthesis Example 1 is repeated, except that 255 mg of (3S,5S)-3-acetylthio-1-allyloxycarbonylpyrrolidin-5-carboxylic acid, 0.93 ml of a 1.1 M Vilsmeier reagent/dichloromethane solution, and 262 mg of 5-allyloxycarbonylaminomethyl-3-(N-methylamino-methyl)imidazo[5,1-b]thiazole are used and 0.145 ml of triethylamine is finally added at 4° C. followed by stirring at room temperature for additional 50 min. Thus, 327.5 mg of the title compound is prepared as a colorless amorphous material.

Workup

  1. customThe procedure of Synthesis Example 1

Sources & evidence

ORD record
ord-13c843c455ee43c0a93c5b606a615bb6
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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