Water → HCID 57855839, compound

HRID 475609Notes

Reaction equation

HRID 475609 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:28])[CH2:9][CH2:10][C:11]1[N:12]=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH:25]([CH3:27])[CH3:26])[CH:17]=2)[O:14][CH:15]=1.C(N(CC)CC)C.[C:36](Cl)(=[O:38])[CH3:37].O>ClCCl>[C:36]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:28])[CH2:9][CH2:10][C:11]1[N:12]=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH:25]([CH3:26])[CH3:27])[CH:17]=2)[O:14][CH:15]=1)(=[O:38])[CH3:37]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 57855862HCID 57855862, compound

Product 1

HCID 57855839HCID 57855839, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 0.2 g quantity of the compound obtained in Example 223 and 0.1 ml of triethylamine were dissolved in 5 ml of dichloromethane, 0.1 ml of acetyl chloride was added to the obtained solution, and the mixture was stirred for 6 hours at room temperature. At the completion of the reaction, water was added to the reaction mixture, and the obtained mixture was extracted with ethyl acetate. The organic layer was washed twice with water, and the solvent was distilled off. The residue was purified using a silica gel column (n-hexane:ethyl acetate=2:1), and the obtained crude crystals were recrystallized with ethanol, thereby yielding 15 mg of white powdery 2-{3-[2-(3-isopropoxy-4-methoxyphenyl)oxazol-4-yl]propionyl}phenyl acetate.

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe obtained mixture was extracted with ethyl acetate
  3. washThe organic layer was washed twice with water
  4. distillationthe solvent was distilled off
  5. customThe residue was purified
  6. customthe obtained crude crystals
  7. customwere recrystallized with ethanol

Sources & evidence

ORD record
ord-5191bc8f468643ea99d5255d4fab64f3
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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