Hydrochloric Acid → HCID 67157926, compound

HRID 550211Notes

Reaction equation

HRID 550211 reaction equation
C([O:3][C:4](=[O:40])[CH2:5][NH:6][CH2:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:20]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[C:27]([CH3:39])[CH:26]=3)([CH2:23][CH3:24])[CH2:21][CH3:22])[CH:16]=2)[CH:11]=1)=[O:9])C.[OH-].[Na+].Cl>C1COCC1.CCO>[CH3:37][C:34]([CH3:35])([CH3:36])[C:33](=[O:38])[CH2:32][O:31][C:28]1[CH:29]=[CH:30][C:25]([C:20]([C:15]2[CH:16]=[C:17]3[C:12](=[CH:13][CH:14]=2)[CH:11]=[C:10]([C:8]([CH2:7][NH:6][CH2:5][C:4]([OH:40])=[O:3])=[O:9])[CH:19]=[CH:18]3)([CH2:23][CH3:24])[CH2:21][CH3:22])=[CH:26][C:27]=1[CH3:39]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67158147HCID 67158147, compound

Product 1

HCID 67157926HCID 67157926, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Treat a solution of [(6-{1-[4-(3,3-Dimethyl-2-oxobutoxy)-3-methylphenyl]-1-ethylpropyl}naphthalene-2-carbonyl)methylamino]acetic acid ethyl ester (0.090 g, 0.16 mmol) in THF (1.25 mL) and EtOH (2.5 mL) with 2N NaOH (0.80 mL, 1.6 mmol). Heat the mixture to 50° C. for 16 h. Acidify the reaction mixture to pH 1 using 1N HCl. Concentrate the resulting mixture. Dilute the residue with EtOAc and water (25 mL each). Separate and discard the aqueous layer. Wash the organic layer with brine, dry over Na2SO4, and filter. Concentrated the filtrate to give the title compound as a white solid (0.070 g, 85%). MS (ES) m/e 518 (M+1).

Workup

  1. concentrationConcentrate the resulting mixture
  2. additionDilute the residue with EtOAc and water (25 mL each)
  3. customSeparate
  4. washWash the organic layer with brine
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. concentrationConcentrated the filtrate

Sources & evidence

ORD record
ord-e74aa1b6330148aabe7e26dd7b80bc89
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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