Hydrochloric Acid → 3-(2-(2-Isopropoxycarbonylamino-ethyl)-4-{2-[5-methyl-2-(4-morpholin-4-yl-phenyl)-oxazol-4-yl]-ethoxy}-phenyl)-propionic acid

HRID 1181090Notes

Reaction equation

HRID 1181090 reaction equation
C[O:2][C:3](=[O:42])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[CH:23][CH:22]=3)[O:18][C:19]=2[CH3:20])=[CH:8][C:7]=1[CH2:33][CH2:34][NH:35][C:36]([O:38][CH:39]([CH3:41])[CH3:40])=[O:37].CO.[Li+].[OH-].Cl>C1COCC1>[CH:39]([O:38][C:36]([NH:35][CH2:34][CH2:33][C:7]1[CH:8]=[C:9]([O:12][CH2:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[CH:23][CH:22]=3)[O:18][C:19]=2[CH3:20])[CH:10]=[CH:11][C:6]=1[CH2:5][CH2:4][C:3]([OH:42])=[O:2])=[O:37])([CH3:41])[CH3:40]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 692310163-(2-(2-Isopropoxycarbonylamino-ethyl)-4-{2-[5-methyl-2-(4-morpholin-4-yl-phenyl)-oxazol-4-yl]-ethoxy}-phenyl)-propionic acid methyl ester

Product 1

HCID 179843243-(2-(2-Isopropoxycarbonylamino-ethyl)-4-{2-[5-methyl-2-(4-morpholin-4-yl-phenyl)-oxazol-4-yl]-ethoxy}-phenyl)-propionic acidYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This ester intermediate was dissolved in THF (0.6 mL) and MeOH (0.4 mL) and treated with aqueous 2M LiOH (1.0 mL, 2.0 mmol). The mixture was stirred for 16 h at ambient temperature, neutralized with HCl (1.0 mL, 2.0 M), and concentrated. The residue was extracted with EtOAc (3×5 mL). The combined organic layers were dried (Na2SO4), concentrated, and purified using silica gel chromatography column (hexanes/EtOAc/HOAc, 5/5/0.02) to afford the title compound (10 mg, 18%). MS (ES+) m/z 566.2 (M+H)+.

Workup

  1. concentrationconcentrated
  2. extractionThe residue was extracted with EtOAc (3×5 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-7f1242fdc81f422d9bba3ce013007223
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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