Water → HCID 131723250, compound

HRID 2185433Notes

Reaction equation

HRID 2185433 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7](=[O:30])[C@@H:8]1[CH2:12][C@H:11](OS(C)(=O)=O)[CH2:10][N:9]1[C:18](=[O:29])[CH2:19][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH3:21].O>CN(C)C=O>[CH3:5][O:6][C:7](=[O:30])[C@@H:8]1[CH2:12][C@@H:11]([N:1]=[N+:2]=[N-:3])[CH2:10][N:9]1[C:18](=[O:29])[CH2:19][N:20]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 21341440HCID 21341440, compound

Product 1

HCID 131723250HCID 131723250, compoundYield 105.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Sodium azide (675 mg) was added to a solution of 1-(N-tert-butoxycarbonyl-N-methylglycyl)-cis-4-methanesulfonyloxy-L-proline methyl ester (B, 0.82 g) in N,N-dimethylformamide (10 mL)-water (1 mL). After stirring at 70° C. for 3 hr, the solvents were removed in vacuo, and the residue was diluted with chloroform. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and evaporated in vacuo to afford the title compound (0.75 g) as a pale yellow oil.

Workup

  1. customthe solvents were removed in vacuo
  2. additionthe residue was diluted with chloroform
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-fe7161e545cf49a6b429ec98bb37daa6
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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