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

HRID 1889269Notes

Reaction equation

HRID 1889269 reaction equation
C[O:2][C:3](=[O:31])[C:4]([CH3:30])([NH:6][C:7]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[O:19][CH:20]([CH3:29])[CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:8])[CH3:5]>C1COCC1.[OH-].[Na+].CO>[CH3:30][C:4]([NH:6][C:7]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[O:19][CH:20]([CH3:29])[CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:8])([CH3:5])[C:3]([OH:31])=[O:2]

Participants

5

Reactant 1

HCID 688437262-Methyl-2-{[1-(1-methyl-2-phenoxy-ethoxy)-naphthalene-2-carbonyl]-amino}-propionic acid methyl ester

Product 1

HCID 578640002-Methyl-2-{[1-(1-methyl-2-phenoxy-ethoxy)-naphthalene-2-carbonyl]-amino}-propionic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

110 mg 2-methyl-2-{[1-(1-methyl-2-phenoxy-ethoxy)-naphthalene-2-carbonyl]-amino}-propionic acid methyl ester in 1 ml THF, 0.3 ml of 2 M sodium hydroxide and 0.3 ml methanol were heated under reflux for 2 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 purification by RP-HPLC 10 mg of 2-methyl-2-{[1-(1-methyl-2-phenoxy-ethoxy)-naphthalene-2-carbonyl]-amino}-propionic acid were obtained.

Workup

  1. temperatureunder reflux for 2 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 purification by RP-HPLC 10 mg of 2-methyl-2-{[1-(1-methyl-2-phenoxy-ethoxy)-naphthalene-2-carbonyl]-amino}-propionic acid
  7. customwere obtained

Sources & evidence

ORD record
ord-c6e6ec263c4645389ee1c2c290173462
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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