Acetic Acid → HCID 67902560, compound

HRID 2352443Notes

Reaction equation

HRID 2352443 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][CH2:23]Cl.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]([CH2:21][O:22][CH3:23])[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 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 11075738HCID 11075738, compound

Product 1

HCID 67902560HCID 67902560, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

4.0 g (93 mmol) sodium hydride (55 percent in oil) was added in 10 portions in 2 hours at -10° C. under argon to a solution of 19 g (77 mmol) of (3as,6aR)[(R)-(1-phenylethyl)]-dihydro-1H-furo-[3,4-d]-imidazol-2,4-(3H,3aH)-dione and 9.42 g (120 mmol) of chloromethyl methyl ether in 200 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 2 ml of acetic acid was added. Then the mixture was evaporated to dryness. Then the residue was taken up in 50 ml of water and 100 ml of dichloromethane, the phases were separated and the aqueous phase was extracted 2 times with 100 ml of dichloromethane. The organic phases were dried over magnesium sulfate and concentrated. After chromatographing the oily residue over silica gel with 500 ml of dichloromethane/ethyl acetate and concentration of the fractions 4.0 g (18 percent) of the title product was obtained as white powder. Concerning the product:

Workup

  1. waitat room temperature for another 2 hours
  2. customThen the mixture was evaporated to dryness
  3. custom100 ml of dichloromethane, the phases were separated
  4. extractionthe aqueous phase was extracted 2 times with 100 ml of dichloromethane
  5. dry with materialThe organic phases were dried over magnesium sulfate
  6. concentrationconcentrated
  7. customwas obtained as white powder

Sources & evidence

ORD record
ord-4b7b2396be8d4b85ba86a288a2c92265
Source dataset
uspto-grants-1989_10
Patent number
US04876350

Reaction notes

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