Acetic Acid → HCID 67909427, compound

HRID 2351814Notes

Reaction equation

HRID 2351814 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:

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-ffc06ab84f684c818244761401b70a64
Source dataset
uspto-grants-1989_10
Patent number
US04873339

Reaction notes

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