2-Methyl-2-{[1-(2-phenoxy-ethoxy)-naphthalene-2-carbonyl]-amino}-butyric acid methyl ester → 2-Methyl-2-{[1-(2-phenoxy-ethoxy)-naphthalene-2-carbonyl]-amino}-butyric acid

HRID 1889265Notes

Reaction equation

HRID 1889265 reaction equation
C[O:2][C:3](=[O:31])[C:4]([CH3:30])([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[O:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:9])[CH2:5][CH3:6]>C1COCC1.[OH-].[Na+].CO>[CH3:30][C:4]([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[O:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:9])([CH2:5][CH3:6])[C:3]([OH:31])=[O:2]

Participants

5

Reactant 1

HCID 688406072-Methyl-2-{[1-(2-phenoxy-ethoxy)-naphthalene-2-carbonyl]-amino}-butyric acid methyl ester

Product 1

HCID 578639872-Methyl-2-{[1-(2-phenoxy-ethoxy)-naphthalene-2-carbonyl]-amino}-butyric acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

419 mg 2-methyl-2-{[1-(2-phenoxy-ethoxy)-naphthalene-2-carbonyl]-amino}-butyric acid methyl ester in 25 ml THF, 1.5 ml of 2 M sodium hydroxide and 8 ml methanol were heated under reflux for 3 h. The organic solvents were then removed in vacuo, and the residue was acidified with 2 M hydrochloric acid and extracted with ethyl acetate twice. The combined organic layers were dried over magnesium sulphate, and concentrated. After recrystallization from toluene 240 mg of 2-methyl-2-{[1-(2-phenoxy-ethoxy)-naphthalene-2-carbonyl]-amino}-butyric acid were obtained.

Workup

  1. temperatureunder reflux for 3 h
  2. customThe organic solvents were then removed in vacuo
  3. extractionextracted with ethyl acetate twice
  4. dry with materialThe combined organic layers were dried over magnesium sulphate
  5. concentrationconcentrated
  6. customAfter recrystallization from toluene 240 mg of 2-methyl-2-{[1-(2-phenoxy-ethoxy)-naphthalene-2-carbonyl]-amino}-butyric acid
  7. customwere obtained

Sources & evidence

ORD record
ord-109bd7507d164bddb304cfdb64477ad7
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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