Water → HCID 67741429, compound

HRID 260233Notes

Reaction equation

HRID 260233 reaction equation
N#N.[C:3]1([S:12]([NH:15][CH2:16][C:17]([NH2:19])=O)(=[O:14])=[O:13])[S:4][CH:5]=[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12.[H-].[Na+].Cl[C:23]([O:25][CH3:26])=[O:24].[OH2:27]>CN(C)C=O>[C:3]1([S:12]([NH:15][C:16](=[O:27])[CH2:17][NH:19][C:23]([O:25][CH3:26])=[O:24])(=[O:14])=[O:13])[S:4][CH:5]=[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 24758Sodium hydride2×HCID 86744696HCID 86744696, compound

Product 1

HCID 67741429HCID 67741429, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product obtained in Step 1 (0.45 g) in N,N-dimethylformamide (5 ml) was added slowly (60% sodium hydride (75 mg) under ice-oooling, and the mixture was stirred for 30 minutes at room temperature. Methyl chloroformate (0.14 ml) was added to the above-mentioned mixture followed by stirring for 20 minutes at room temperature. 60% sodium hydride (75 mg) was added to the solution, and the mixture was stirred for 1.5 hours at room temperature, then 15 minutes at 70° C. After cooling to room temperature, water (20 ml) was added to the resultant mixture and this aqueous solution was extracted with ethyl acetate (20 ml×3). The organic layer was washed with water, then saturated aqueous NaCl solution. After drying over anhydrous magnesium sulfate, ethyl acetate was removed in vacuo and the residue was purified by silica-gel columun chromatography to give 0.18 g of the objective compound.

Workup

  1. stirringby stirring for 20 minutes at room temperature
  2. stirringthe mixture was stirred for 1.5 hours at room temperature
  3. custom15 minutes
  4. customat 70° C
  5. temperatureAfter cooling to room temperature
  6. extractionthis aqueous solution was extracted with ethyl acetate (20 ml×3)
  7. washThe organic layer was washed with water
  8. dry with materialAfter drying over anhydrous magnesium sulfate, ethyl acetate
  9. customwas removed in vacuo
  10. customthe residue was purified by silica-gel columun chromatography

Sources & evidence

ORD record
ord-67ae2efdcc4044af982075bec0ce9181
Source dataset
uspto-grants-1996_06
Patent number
USRE035279

Reaction notes

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