Citric Acid → HCID 58691261, compound

HRID 602336Notes

Reaction equation

HRID 602336 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][C@H:7]1[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@@H:9]([C:19](=[O:34])[NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][C:28]3=[O:33])=[CH:23][CH:22]=2)[CH2:8]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>N1C=CC=CC=1>[CH3:1][S:2]([O:6][C@H:7]1[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@@H:9]([C:19](=[O:34])[NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][C:28]3=[O:33])=[CH:23][CH:22]=2)[CH2:8]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 31297Methanesulfonyl chlorideHCID 66593297HCID 66593297, compound

Product 1

HCID 58691261HCID 58691261, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

9.1 1.3 ml (16.65 mmol) of methanesulfonyl chloride are added dropwise with ice cooling to a solution of 4.5 g (11.1 mmol) of tert-butyl (2R,4R)-4-hydroxy-2-[4-(3-oxomorpholin-4-yl)phenylcarbamoyl]pyrrolidine-1-carboxylate in 20 ml of pyridine, and the reaction solution is stirred at room temperature for 12 hours. The pyridine is subsequently stripped off under reduced pressure, 10 ml of saturated citric acid solution are added to the residue, and the acidic solution is extracted twice with 10 ml of methylene chloride each time. The combined organic phases are then washed with 10 ml of saturated sodium chloride solution and dried over sodium sulfate. Removal of the drying agent by filtration and stripping-off of the solvent gives 5.4 g (100%) of tert-butyl (2R,4R)-4-methanesulfonyloxy-2-[4-(3-oxomorpholin-4-yl)phenylcarbamoyl]pyrrolidine-1-carboxylate as a yellow oil, ESI 484.

Workup

  1. additionare added to the residue
  2. extractionthe acidic solution is extracted twice with 10 ml of methylene chloride each time
  3. washThe combined organic phases are then washed with 10 ml of saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the drying agent
  6. filtrationby filtration

Sources & evidence

ORD record
ord-2019657259924ee5ac7c1a20dcefba65
Source dataset
uspto-grants-2011_03
Patent number
US07906516B2

Reaction notes

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