Dimethylformamide → HCID 86759765, compound

HRID 1072349Notes

Reaction equation

HRID 1072349 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[O:8])[C@H:4]([C:20]([C:22]2[N:23]=[CH:24][N:25]3[CH:29]=[CH:28][S:27][C:26]=23)=[O:21])[CH2:3]1.CN(C=O)C.C(N(CC)CC)C.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>ClCCl.O>[CH3:42][S:43]([O:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[O:8])[C@H:4]([C:20]([C:22]2[N:23]=[CH:24][N:25]3[CH:29]=[CH:28][S:27][C:26]=23)=[O:21])[CH2:3]1)(=[O:45])=[O:44]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69364253HCID 69364253, compound

Product 1

HCID 86759765HCID 86759765, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

7-[(2S,4R)-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-2-yl]carbonylimidazo[5,1-b]thiazole (850 mg) was dissolved in 20 ml of dichloromethane and 7 ml of DMF under ice cooling to prepare a solution. Triethylamine (0.425 ml) and 0.19 ml of methanesulfonyl chloride were added to the solution, and the mixture was stirred for 30 min. Water was added to the reaction solution, and the mixture was extracted with dichloromethane, followed by washing twice with brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then removed by distillation to give 734 mg of a crude product of 7-[(2S,4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-2-yl]carbonylimidazo[5,1-b]thiazole.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washby washing twice with brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was then removed by distillation

Sources & evidence

ORD record
ord-d65dd9f8d5dd4befbd9d00ffe9bcce53
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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