HCID 19352271, compound → HCID 19352273, compound

HRID 1636643Notes

Reaction equation

HRID 1636643 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[C:7](=[O:21])[O:8][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[C:12]=2[O:19][CH3:20])[CH:10]=1)=[O:4]>[Pd].CO>[CH3:1][O:2][C:3]([NH:5][CH:6]([CH2:10][CH2:9][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[C:12]=1[O:19][CH3:20])[C:7]([OH:21])=[O:8])=[O:4]

Participants

4

Reactant 1

HCID 19352271HCID 19352271, compound

Product 1

HCID 19352273HCID 19352273, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
64 °C

Procedure

150 g of 3-methoxycarbonylamino-5(2,3-dimethoxyphenyl)-2,5-dihydro-furan-2-one and 1190 ml of CH3OH are placed into 2000 ml flasks of a Parr hydrogenator, then they are heated until complete dissolution with stirring (T about 64° C.); 30 g of 5% Pd/C are added and hydrogenation is started at 35 psi until H2 is no longer absorbed (about 60 minutes). The disappearance of the starting compound is checked by TLC, then the mixture is filtered through Celite and the filtrate is evaporated to dryness, the resulting oil is precipitated with stirring by adding ethyl ether and petroleum ether, stirring is continued for about 30 minutes, then the mixture is filtered and dried under vacuum at 60° C. 141.6 g are obtained. (Yield 93%).

Workup

  1. temperaturethey are heated until complete dissolution
  2. customis no longer absorbed (about 60 minutes)
  3. filtrationthe mixture is filtered through Celite
  4. customthe filtrate is evaporated to dryness
  5. customthe resulting oil is precipitated
  6. stirringwith stirring
  7. additionby adding ethyl ether and petroleum ether
  8. stirringstirring
  9. filtrationthe mixture is filtered
  10. customdried under vacuum at 60° C
  11. custom141.6 g are obtained

Sources & evidence

ORD record
ord-b5e8dca639c9465cb5380b0bedd62418
Source dataset
uspto-grants-2000_03
Patent number
US06034277

Reaction notes

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