Sodium Hydroxide → HCID 178436706, compound

HRID 1533444Notes

Reaction equation

HRID 1533444 reaction equation
[OH-].[Na+].[CH2:3]([C:5]1[CH:9]=[C:8]([C:10]([O:12]CC)=[O:11])[NH:7][N:6]=1)[CH3:4]>CO>[CH2:3]([C:5]1[CH:9]=[C:8]([C:10]([OH:12])=[O:11])[NH:7][N:6]=1)[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178468923HCID 178468923, compound

Product 1

HCID 178436706HCID 178436706, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous sodium hydroxide solution (10 M; 100 ml, 1.0 mol) was added dropwise to a stirred suspension of the title compound of example (4a) (66.0 g, 0.39 mol) in methanol and the resulting solution heated under reflux for 4 hours. The cool reaction mixture was concentrated under reduced pressure to ca. 200 ml, diluted with water (200 ml) and this mixture washed with toluene (3×100 ml). The resulting aqueous phase was acidified with concentrated hydrochloric acid to pH 4 and the white precipitate collected and dried by suction to provide the title compound (34.1 g). δ (DMSOd6): 1.13 (3H,t), 2.56 (2H,q), 6.42 (1H,s).

Workup

  1. temperaturethe resulting solution heated
  2. temperatureunder reflux for 4 hours
  3. customThe cool reaction mixture
  4. concentrationwas concentrated under reduced pressure to ca. 200 ml
  5. additiondiluted with water (200 ml)
  6. washthis mixture washed with toluene (3×100 ml)
  7. customthe white precipitate collected
  8. customdried by suction

Sources & evidence

ORD record
ord-da6b2eea533c4bb295b0368f388e616c
Source dataset
uspto-grants-2001_03
Patent number
US06207829B1

Reaction notes

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