Sodium Hydroxide → HCID 68841684, compound

HRID 1889288Notes

Reaction equation

HRID 1889288 reaction equation
C[O:2][C:3](=[O:30])[C:4]([CH3:29])([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[CH:19]=[CH:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:8])[CH3:5].[OH-].[Na+]>CO.C1COCC1>[CH3:29][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[CH:19]=[CH:20][CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:8])([CH3:5])[C:3]([OH:30])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68841966HCID 68841966, compound

Product 1

HCID 68841684HCID 68841684, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

80 mg of a mixture of the (E)- and (Z)-isomers of 2-methyl-2-{[1-(4-phenyl-but-1-enyl)-naphthalene-2-carbonyl]-amino}-propionic acid methyl ester were reacted with 0.5 ml of 2 M sodium hydroxide in 1 ml methanol and 2 ml THF for 15 min at 60° C. The organic solvents were removed in vacuo, the mixture was acidified with 2 M hydrochloric acid and extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over magnesium sulphate and concentrated to yield 75 mg of a mixture of the (E)- and (Z)-isomers of 2-methyl-2-{[1-(4-phenyl-but-1-enyl)-naphthalene-2-carbonyl]-amino}-propionic acid.

Workup

  1. customThe organic solvents were removed in vacuo
  2. extractionextracted with ethyl acetate twice
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fc0b2da387d344da9ce045c2e5d585f6
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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