Sodium Hydroxide → 3-(3-Fluoro-4-{1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-heptyloxy}-benzoylamino)-propionic acid

HRID 1669326Notes

Reaction equation

HRID 1669326 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:42])[CH2:6][CH2:7][NH:8][C:9](=[O:41])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:17]([C:24]2[CH:25]=[N:26][C:27]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=3)=[CH:28][CH:29]=2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:12]([F:40])[CH:11]=1>CO>[F:40][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[O:16][CH:17]([C:24]1[CH:25]=[N:26][C:27]([C:30]2[CH:31]=[CH:32][C:33]([C:36]([F:39])([F:37])[F:38])=[CH:34][CH:35]=2)=[CH:28][CH:29]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:9]([NH:8][CH2:7][CH2:6][C:5]([OH:42])=[O:4])=[O:41]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 673417153-(3-Fluoro-4-{1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-heptyloxy}-benzoylamino)-propionic acid methyl ester

Product 1

HCID 597294493-(3-Fluoro-4-{1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-heptyloxy}-benzoylamino)-propionic acidYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add sodium hydroxide (5.0N, 0.07 mL, 0.34 mmol) to 3-(3-fluoro-4-{1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-heptyloxy}-benzoylamino)-propionic acid methyl ester (0.038 g, 0.07 mmol) in methanol (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 0.025 g (66%) of title compound. MS (ESI) m/z 547.2 (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-04d395afacd04931a845f47aaed5cd0c
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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