Sodium Hydroxide → 3-{3-Fluoro-4-[1-(4'-trifluoromethyl-biphenyl-4-yl)-heptyloxy]-benzoylamino}-propionic acid

HRID 1669336Notes

Reaction equation

HRID 1669336 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:43])[CH2:7][CH2:8][NH:9][C:10](=[O:42])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=3)=[CH:27][CH:26]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:13]([F:41])[CH:12]=1)C>C(O)C>[F:41][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][C:14]=1[O:17][CH:18]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:32]=[CH:33][C:34]([C:37]([F:38])([F:39])[F:40])=[CH:35][CH:36]=2)=[CH:27][CH:26]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:10]([NH:9][CH2:8][CH2:7][C:6]([OH:43])=[O:5])=[O:42]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 597293873-{3-Fluoro-4-[1-(4'-trifluoromethyl-biphenyl-4-yl)-heptyloxy]-benzoylamino}-propionic acid ethyl ester

Product 1

HCID 116063533-{3-Fluoro-4-[1-(4'-trifluoromethyl-biphenyl-4-yl)-heptyloxy]-benzoylamino}-propionic acidYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add sodium hydroxide (5.0N, 0.03 mL, 0.15 mmol) to 3-{3-fluoro-4-[1-(4′-trifluoromethyl-biphenyl-4-yl)-heptyloxy]-benzoylamino}-propionic acid ethyl ester (0.0172 g, 0.03 mmol) in ethanol (0.5 mL) and stir for three hours. Acidify with 1.0 N HCl and extract desired compound with ethyl acetate three times. Dry organic fractions with Na2SO4, filter and concentrate under reduced pressure to provide 0.015 g (92%) of title compound. MS (ESI) m/z 546.3 [M+H]+.

Workup

  1. extractionAcidify with 1.0 N HCl and extract desired compound with ethyl acetate three times
  2. filtrationDry organic fractions with Na2SO4, filter
  3. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-8abbf4c3e1154683863fbc0ce5e98878
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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