Hydrochloric Acid → 3-{4-[1-(4'-Isopropyl-2-methyl-biphenyl-4-yl)-5-methyl-hexyloxy]-benzoylamino}-propionic acid

HRID 1669332Notes

Reaction equation

HRID 1669332 reaction equation
C[O:2][C:3](=[O:39])[CH2:4][CH2:5][NH:6][C:7](=[O:38])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:15]([C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][C:31]([CH:34]([CH3:36])[CH3:35])=[CH:30][CH:29]=3)=[C:24]([CH3:37])[CH:23]=2)[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:10][CH:9]=1.[OH-].[Na+].Cl>C1COCC1>[CH:34]([C:31]1[CH:30]=[CH:29][C:28]([C:25]2[CH:26]=[CH:27][C:22]([CH:15]([O:14][C:11]3[CH:10]=[CH:9][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:39])=[O:2])=[O:38])=[CH:13][CH:12]=3)[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:23][C:24]=2[CH3:37])=[CH:33][CH:32]=1)([CH3:35])[CH3:36]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 673432783-{4-[1-(4'-Isopropyl-2-methyl-biphenyl-4-yl)-5-methyl-hexyloxy]-benzoylamino}-propionic acid methyl ester

Product 1

HCID 597293793-{4-[1-(4'-Isopropyl-2-methyl-biphenyl-4-yl)-5-methyl-hexyloxy]-benzoylamino}-propionic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-{4-[1-(4′-Isopropyl-2-methyl-biphenyl-4-yl)-5-methyl-hexyloxy]-benzoylamino}-propionic acid methyl ester (50 mg) was taken into THF (1.0 mL) and treated with NaOH (1.0 mL, 5.0 N), then refluxed under nitrogen. The reaction mixture was neutralized with HCl (1.0 mL, 5.0 N), extracted with ethyl ether, dried over sodium sulfate. Concentration gave the title compound. MS (ES): 516.7 [M+H]+, the structure was also confirmed by proton NMR.

Workup

  1. temperaturerefluxed under nitrogen
  2. extractionextracted with ethyl ether
  3. dry with materialdried over sodium sulfate
  4. concentrationConcentration

Sources & evidence

ORD record
ord-457f48026f6644b88d4d21c62128016c
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

Loading…