Hydrochloric Acid → HCID 11961321, compound

HRID 2375739Notes

Reaction equation

HRID 2375739 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:37])[CH2:7][C@@H:8]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[CH:24]=[C:25]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=3[CH3:36])[CH:26]=[CH:27][CH:28]=2)=[CH:17][CH:16]=1)[C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1)C.Cl>CCO>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([CH2:22][O:21][C:18]3[CH:17]=[CH:16][C:15]([C@@H:8]([C:9]4[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=4)[CH2:7][C:6]([OH:37])=[O:5])=[CH:20][CH:19]=3)[CH:24]=2)=[C:30]([CH3:36])[CH:31]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58758897HCID 58758897, compound

Product 1

HCID 11961321HCID 11961321, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10% NaOH (aq) (1 mL) was added to a solution of (S)-ethyl 3-(4-[3-(4-chloro-2-methylphenyl)benzyloxy]phenyl)-3-(1-methyl-1H-imidazol-2-yl)propanoate (9.10) (49 mg, 0.1 mmol) in EtOH (2 mL). The reaction mixture was stirred at room temperature for 4 hours. 1N HCl was added to neutralize the mixture to pH 6-7. The mixture was extracted with EtOAc (2×20 mL), washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was flash chromatographed (silica gel, 0-10% MeOH in DCM) to afford (S)-3-[4-(4′-chloro-2′-methyl-biphenyl-3-ylmethoxy)-phenyl]-3-(1-methyl-1H-imidazol-2-yl)-propionic acid (9) as a colorless oil. MS ESI (neg.) m/e: 459 (M−H). 1H NMR (500 MHz) (DMSO) δ 7.87 (broad s, 1H); 6.63-7.46 (m, 13H); 5.06 (s, 2H); 4.49 (dd, J=8.4, 3.2 Hz, 1H); 3.39 (s, 3H); 3.29 (dd, J=15.0, 8.5 Hz, 1H); 3.10 (dd, J=15.2, 3.0 Hz, 1H); 2.23 (s, 3H).

Workup

  1. extractionThe mixture was extracted with EtOAc (2×20 mL)
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customchromatographed (silica gel, 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-1130c266c8e24fcdb5601b64bf3ef698
Source dataset
uspto-grants-2008_12
Patent number
US07465804B2

Reaction notes

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