Sodium Hydroxide → HCID 57864065, compound

HRID 1889282Notes

Reaction equation

HRID 1889282 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[C:19]#[C: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[C:19]#[C: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 68840871HCID 68840871, compound

Product 1

HCID 57864065HCID 57864065, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

20 mg 2-methyl-2-{[1-(4-phenyl-but-1-ynyl)-naphthalene-2-carbonyl]-amino}-propionic acid methyl ester were reacted with 60 μl of 2 M sodium hydroxide in 0.5 ml methanol and 0.5 ml THF for 48 h room temperature and for 4 h at 60° C. The organic solvents were then removed in vacuo, and the residue was treated with water, acidified with 2 M hydrochloric acid and extracted with ethyl acetate twice. The combined organic layers were dried over sodium sulphate, and concentrated. After chromatography on silica (ethyl acetate/heptane) 11 mg of 2-methyl-2-{[1-(4-phenyl-but-1-ynyl)-naphthalene-2-carbonyl]-amino}-propionic acid were obtained.

Workup

  1. customThe organic solvents were then removed in vacuo
  2. additionthe residue was treated with water
  3. extractionextracted with ethyl acetate twice
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5a6170489911474880ad59e5eba79509
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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