Hydrochloric Acid → 2-(3-(4-(3-p-Tolylureido)phenyl)isoxazole-5-carboxamido)acrylic acid

HRID 75836Notes

Reaction equation

HRID 75836 reaction equation
[C:1]1([CH3:31])[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:30])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:20]=[C:19]([C:21]([NH:23][C:24](=[CH2:29])[C:25]([O:27]C)=[O:26])=[O:22])[O:18][N:17]=3)=[CH:12][CH:11]=2)=[CH:3][CH:2]=1.O.O.[OH-].[Li+].Cl>C1COCC1>[C:1]1([CH3:31])[CH:2]=[CH:3][C:4]([NH:7][C:8](=[O:30])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:20]=[C:19]([C:21]([NH:23][C:24](=[CH2:29])[C:25]([OH:27])=[O:26])=[O:22])[O:18][N:17]=3)=[CH:12][CH:11]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67353451HCID 67353451, compound

Product 1

HCID 673532812-(3-(4-(3-p-Tolylureido)phenyl)isoxazole-5-carboxamido)acrylic acidYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(3-(4-(3-p-tolylureido)phenyl)isoxazole-5-carboxamido)acrylate (125 mg, 0.298 mmol) was dissolved in THF and water in 2:1 ratio. Lithium hydroxide monohydrate (19 mg, 0.447 mmol) was added and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was acidified with dilute HCl and extracted with EtOAc. Organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure. Crude compound was purified by washing with methanol to get 60 mg (50%) white solid as the required compound. MS: ES (+): m/z 407(M+1); 1HNMR (DMSO-d6, 300 MHz) δ: 9.732 (s, 1H), 8.989 (s, 1H), 8.714 (s, 1H), 7.894 (d, 2H), 7.784 (s, 1H), 7.638 (d, 2H), 7.377 (d, 2H), 7.121 (d, 2H), 6.232 (s, 1H), 5.921 (s, 1H), 5.918 (s, 3H).

Workup

  1. extractionextracted with EtOAc
  2. customOrganic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customCrude compound was purified
  6. washby washing with methanol

Sources & evidence

ORD record
ord-0951b442520e458eb5b4c668149fce9a
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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