Acetic Acid → HCID 18925261, compound

HRID 1289045Notes

Reaction equation

HRID 1289045 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]([CH2:25][CH3:26])[C:12](=[O:27])[NH:11][C:10]1=[O:28])(=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]([CH2:25][CH3:26])[C:12](=[O:27])[NH:11][C:10]1=[O:28]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 18925217HCID 18925217, compound

Product 1

HCID 18925261HCID 18925261, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 50 mg (0.13 mmol) of the compound obtained from Example 80 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 26 mg (yield 56%) of the title compound as a white solid.

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-23b2c62486504e1eaf60f8ae35481b06
Source dataset
uspto-grants-1998_05
Patent number
US05747500

Reaction notes

Loading…