Sodium Hydroxide → 3-{3-Fluoro-4-[1-(2-methyl-4'-trifluoromethyl-biphenyl-4-yl)-heptyloxy]-benzoylamino}-propionic acid

HRID 1669342Notes

Reaction equation

HRID 1669342 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:44])[CH2:7][CH2:8][NH:9][C:10](=[O:43])[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)=[C:27]([CH3:41])[CH:26]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:13]([F:42])[CH:12]=1)C>C(O)C>[F:42][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:36]=[CH:35][C:34]([C:37]([F:38])([F:39])[F:40])=[CH:33][CH:32]=2)=[C:27]([CH3:41])[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:44])=[O:5])=[O:43]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 597294083-{3-Fluoro-4-[1-(2-methyl-4'-trifluoromethyl-biphenyl-4-yl)-heptyloxy]-benzoylamino}-propionic acid ethyl ester

Product 1

HCID 597293823-{3-Fluoro-4-[1-(2-methyl-4'-trifluoromethyl-biphenyl-4-yl)-heptyloxy]-benzoylamino}-propionic acidYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add sodium hydroxide (5.0N, 0.03 mL, 0.15 mmol) to 3-{3-Fluoro-4-[1-(2-methyl-4′-trifluoromethyl-biphenyl-4-yl)-heptyloxy]-benzoylamino}-propionic acid ethyl ester (0.024 g, 0.041 mmol) in ethanol (5 mL) and stir for three hours. Acidify with 1.0 N HCl and extract desired compound with ethyl acetate three times. Wash organic phase with saturated sodium chloride solution, dry over Na2SO4, filter, and concentrate under reduced pressure to provide 0.019 g (83%) of title compound. MS (ESI) m/z 560.2 [M+H]+.

Workup

  1. extractionAcidify with 1.0 N HCl and extract desired compound with ethyl acetate three times
  2. dry with materialWash organic phase with saturated sodium chloride solution, dry over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-d29c8c1677c741b69a20b1b3a7964524
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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