Hydrochloric Acid → 3-(4-(3-(2-Fluorophenyl)ureido)phenyl)isoxazole-5-carboxylic acid

HRID 75816Notes

Reaction equation

HRID 75816 reaction equation
C([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])=[O:19])=[CH:13][CH:12]=2)[CH:7]=1)=[O:5])C.[OH-].[Na+].Cl>C1COCC1>[F:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[NH:20][C:18](=[O:19])[NH:17][C:14]1[CH:13]=[CH:12][C:11]([C:8]2[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[O:10][N:9]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 673543933-{4-[3-(2-Fluoro-phenyl)ureido]-phenyl}-isoxazole-5-carboxylic acid ethyl ester

Product 1

HCID 673539813-(4-(3-(2-Fluorophenyl)ureido)phenyl)isoxazole-5-carboxylic acidYield 86.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-{4-[3-(2-Fluoro-phenyl)ureido]-phenyl}-isoxazole-5-carboxylic acid ethyl ester (4.6 g) was dissolved in THF (92 ml). 1M aqueous NaOH solution (65 ml) was added and stirred at RT for 15-20 minutes. The reaction mixture was acidified with dilute HCl and extracted with EtOAc. Organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure to get off white solid, which was crystallized from CH2Cl2 to yield 3.68 g (86%) white solid. MS (ES+): m/z 342 (M+1); 1HNMR (DMSO-d6, 300 MHz): δ 9.33 (s, 1H), 8.63 (s, 1H), 8.13 (m, 1H), 7.89 (d, 2H), 7.7 (s, 1H), 7.6 (d, 2H), 7.23 (m, 1H), 7.13 (m, 1H), 7.02 (m, 1H).

Workup

  1. extractionextracted with EtOAc
  2. customOrganic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get off white solid, which
  6. customwas crystallized from CH2Cl2

Sources & evidence

ORD record
ord-8f8e0ba9569b4b31826f39b52805b5b3
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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