Sodium hydride → HCID 58691259, compound

HRID 602350Notes

Reaction equation

HRID 602350 reaction equation
[H-].[Na+].[CH3:3][O:4][C@H:5]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@@H:7]([C:17](=[O:32])[NH:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][C:26]3=[O:31])=[CH:21][CH:20]=2)[CH2:6]1.Br[CH2:34][C:35]([O:37][CH3:38])=[O:36]>CN(C)C=O>[CH3:3][O:4][C@H:5]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:11])[C@@H:7]([C:17](=[O:32])[N:18]([CH2:34][C:35]([O:37][CH3:38])=[O:36])[C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][C:26]3=[O:31])=[CH:21][CH:20]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 58691278HCID 58691278, compound

Product 1

HCID 58691259HCID 58691259, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

61 mg (2.54 mmol) of sodium hydride are added to the solution of 1 g (2.31 mmol) of tert-butyl (2R,4R)-4-methoxy-2-[4-(3-oxomorpholin-4-yl)-phenylcarbamoyl]pyrrolidine-1-carboxylate (prepared analogously to Example 7.1) in 20 ml of dimethylformamide, and the mixture is stirred at room temperature for 30 minutes. 0.22 mg (2.31 mmol) of methyl bromoacetate is subsequently added to the reaction mixture, which is then left to stir at room temperature for 12 hours. The reaction mixture is then evaporated under reduced pressure, the residue is taken up in 20 ml of water, and the aqueous solution is extracted three times with 20 ml of methylene chloride each time. Drying of the combined organic phases over sodium sulfate and stripping-off of the solvent gives 1.1 g of tert-butyl (2R,4R)-4-methoxy-2-{methoxycarbonylmethyl-[4-(3-oxomorpholin-4-yl)phenyl]-carbamoyl}pyrrolidine-1-carboxylate as a yellow oil; ESI (M-BOC) 392.

Workup

  1. waitis then left
  2. stirringto stir at room temperature for 12 hours
  3. customThe reaction mixture is then evaporated under reduced pressure
  4. extractionthe aqueous solution is extracted three times with 20 ml of methylene chloride each time
  5. dry with materialDrying of the combined organic phases over sodium sulfate and stripping-off of the solvent

Sources & evidence

ORD record
ord-507b3a2198604a019d50db853c729477
Source dataset
uspto-grants-2011_03
Patent number
US07906516B2

Reaction notes

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