Acetic Acid → HCID 67909427, compound

HRID 373400Notes

Reaction equation

HRID 373400 reaction equation
[H-].[Na+].[C:3]1([C@H:9]([N:11]2[C@H:15]3[CH2:16][O:17][C:18](=[O:19])[C@H:14]3[NH:13][C:12]2=[O:20])[CH3:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:21][O:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][CH:24]=1.C(O)(=O)C>CN(C)C=O>[C:3]1([C@H:9]([N:11]2[C@H:15]3[CH2:16][O:17][C:18](=[O:19])[C@H:14]3[N:13]([CH2:27][C:26]3[CH:29]=[CH:30][C:23]([O:22][CH3:21])=[CH:24][CH:25]=3)[C:12]2=[O:20])[CH3:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 11075738HCID 11075738, compound

Product 1

HCID 67909427HCID 67909427, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

9.75 g (0.22 mol) of sodium hydride (55 percent in oil) was added in 10 portions in 2 hours at -10° C. under argon to a solution of 50.0 g (0.2 mol) of (3aS, 6aR)-1-[(R)-(1-phenylethyl)]-dihydro-1H-furo-[3,4-d] -imidazol-2,4-(3H, 3aH)-dione and 39.8 g (0.25 mol) of 4-methoxybenzyl chloride in 500 ml of dried N,N-dimethylformamide. The reaction mixture was stirred at 5° C. for 2 hours and then at room temperature for another 2 hours. Then 8 ml of acetic acid was added. Then the mixture was evaporated to dryness. Then the residue was taken up in 100 ml of water and 200 ml of dichloromethane, the phases were separated and the aqueous phase was extracted twice with 100 ml of dichloromethane. The organic phases were dried over magnesium sulfate and concentrated. After suspension in ethanol with refluxing, cooling and filtering, 53.5 g (72 percent) of the title product was obtained in the form of white needles. Concerning the product: Melting point: 146.1°-146.4° C.

Workup

  1. waitat room temperature for another 2 hours
  2. customThen the mixture was evaporated to dryness
  3. custom200 ml of dichloromethane, the phases were separated
  4. extractionthe aqueous phase was extracted twice with 100 ml of dichloromethane
  5. dry with materialThe organic phases were dried over magnesium sulfate
  6. concentrationconcentrated
  7. temperatureAfter suspension in ethanol with refluxing
  8. temperaturecooling
  9. filtrationfiltering

Sources & evidence

ORD record
ord-f3c43c7a2ea747b58d52902291e77a7b
Source dataset
uspto-grants-1992_11
Patent number
US05162540

Reaction notes

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