Hydrochloric Acid → 3-{4-[1-(4'-Trifluoromethyl-biphenyl-4-ylmethyl)-propoxy]-benzoylamino}-propionic acid

HRID 1669293Notes

Reaction equation

HRID 1669293 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][CH2:5][NH:6][C:7](=[O:35])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:15]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)[CH2:16][CH3:17])=[CH:10][CH:9]=1.[OH-].[Na+].Cl>CO>[F:32][C:31]([F:33])([F:34])[C:28]1[CH:27]=[CH:26][C:25]([C:22]2[CH:23]=[CH:24][C:19]([CH2:18][CH:15]([O:14][C:11]3[CH:10]=[CH:9][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:36])=[O:2])=[O:35])=[CH:13][CH:12]=3)[CH2:16][CH3:17])=[CH:20][CH:21]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 673430863-{4-[1-(4'-Trifluoromethyl-biphenyl-4-ylmethyl)-propoxy]-benzoylamino}-propionic acid methyl ester

Product 1

HCID 115187043-{4-[1-(4'-Trifluoromethyl-biphenyl-4-ylmethyl)-propoxy]-benzoylamino}-propionic acidYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-{4-[1-(4′-trifluoromethyl-biphenyl-4-ylmethyl)-propoxy]-benzoylamino}-propionic acid methyl ester (0.012 g, 0.02 mmol) in methanol (1 mL) is added sodium hydroxide (5.0N, 0.02 mL, 0.12 mmol) and stirred for three hours. The mixture is acidified with 1.0 N HCl and extracted with ethyl acetate three times. Organic layers are dried over sodium sulfate, filtered and concentrated under reduced pressure provided 0.009 g (0.019 mmol, 77%) of title compound. MS (ESI) m/z 486.2 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialOrganic layers are dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-241d61aacb494fcf869977dd6ca66f05
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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