Methanol → HCID 86730092, compound

HRID 523943Notes

Reaction equation

HRID 523943 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:24]=[C:25]([N+:27]([O-])=O)[CH:26]=2)[O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([CH3:23])([CH3:22])[C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.CO>C(OCC)(=O)C>[NH2:27][C:25]1[CH:24]=[C:9]([CH:8]=[C:7]([O:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:31][CH:30]=2)[CH:26]=1)[O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH3:22])([CH3:23])[C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 86730093HCID 86730093, compound

Product 1

HCID 86730092HCID 86730092, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under an argon atmosphere, to a 500-mL pear-shaped evaporating flask was added the compound prepared in Example 5 (53.6 g) to which a mixed solution of methanol (50 mL) and ethyl acetate (175 mL) was added. The mixture was heated until dissolution, and the flask was purged with argon prior to addition of 5% palladium carbon (10.8 g). The flask was degassed and charged with hydrogen gas. The flask was vigorously stirred at room temperature for 3 hours. The reaction system was purged with argon, filtered with celite and washed with ethyl acetate. The obtained filtrate was subjected to distillation under reduced pressure to give the titled compound (43.9 g) having the following physical properties.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated until dissolution
  3. customthe flask was purged with argon
  4. additionto addition of 5% palladium carbon (10.8 g)
  5. customThe flask was degassed
  6. additioncharged with hydrogen gas
  7. customThe reaction system was purged with argon
  8. filtrationfiltered with celite
  9. washwashed with ethyl acetate
  10. distillationThe obtained filtrate was subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-99b45558517e4c0bb63da236cbf40f4e
Source dataset
uspto-grants-2016_05
Patent number
US09340499B2

Reaction notes

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