Acetic Acid → HCID 18925249, compound

HRID 1289044Notes

Reaction equation

HRID 1289044 reaction equation
C([O:4][CH2:5]/[CH:6]=[CH:7]/[CH2:8][N:9]1[C:14]([C:15](=[O:24])[C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=2)=[C:13]([CH:25]([CH3:27])[CH3:26])[C:12](=[O:28])[NH:11][C:10]1=[O:29])(=O)C.C[O-].[Na+].C(O)(=O)C>CO>[OH:4][CH2:5]/[CH:6]=[CH:7]/[CH2:8][N:9]1[C:14]([C:15](=[O:24])[C:16]2[CH:17]=[C:18]([CH3:23])[CH:19]=[C:20]([CH3:22])[CH:21]=2)=[C:13]([CH:25]([CH3:26])[CH3:27])[C:12](=[O:28])[NH:11][C:10]1=[O:29]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 18925246HCID 18925246, compound

Product 1

HCID 18925249HCID 18925249, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 80 mg (0.2 mmol) of the compound obtained from Example 75 in 5 ml of methanol was added 20 mg (0.37 mmol) of sodium methoxide at room temperature. After 1 hour, the reaction mixture was neutralized with acetic acid and evaporated under reduced pressure to give a yellow-colored residue, which was purified by flash chromatography using a mixture of ethyl acetate and hexane (4:1) as an eluent to afford 60 mg (yield 82%) of the title compound as a colorless syrup.

Workup

  1. customevaporated under reduced pressure
  2. customto give a yellow-colored residue, which
  3. customwas purified by flash chromatography
  4. additiona mixture of ethyl acetate and hexane (4:1) as an eluent

Sources & evidence

ORD record
ord-960645018fe04c24ba1f2cbe96fee087
Source dataset
uspto-grants-1998_05
Patent number
US05747500

Reaction notes

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