Ethyl Acetate → [4-[[2-(3-Benzyl-ureido)-thiazole-4-carbonyl]-amino]-phenoxy]-acetic acid

HRID 378998Notes

Reaction equation

HRID 378998 reaction equation
[CH2:1]([NH:8][C:9](=[O:32])[NH:10][C:11]1[S:12][CH:13]=[C:14]([C:16]([NH:18][C:19]2[CH:31]=[CH:30][C:22]([O:23][CH2:24][C:25]([O:27]CC)=[O:26])=[CH:21][CH:20]=2)=[O:17])[N:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(OCC)(=O)C>C(O)C>[CH2:1]([NH:8][C:9](=[O:32])[NH:10][C:11]1[S:12][CH:13]=[C:14]([C:16]([NH:18][C:19]2[CH:31]=[CH:30][C:22]([O:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:21][CH:20]=2)=[O:17])[N:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 54538745Ethyl (4-{[2-(3-benzyl-ureido)-thiazole-4-carbonyl]-amino}-phenoxy)-acetate

Product 1

HCID 21697704[4-[[2-(3-Benzyl-ureido)-thiazole-4-carbonyl]-amino]-phenoxy]-acetic acidYield 91.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

243 mg of ethyl (4-{[2-(3-benzyl-ureido)-thiazole-4-carbonyl]-amino}-phenoxy)-acetate are stirred in 4.3 ml of ethanol and 0.8 ml of 1N NaOH for 4.5 hrs. at RT. For the working up, the mixture is stirred into ethyl acetate/dilute hydrochloric acid, the organic phase is separated, washed with water and sodium chloride solution, dried over sodium sulphate dried and evaporated in a vacuum. Crystallization from ether gives 208 mg of [4-[[2-(3-benzyl-ureido)-thiazole-4-carbonyl]-amino]-phenoxy]-acetic acid, m.p. 208° C., MS: 427 (M+H)+.

Workup

  1. customat RT
  2. customthe organic phase is separated
  3. washwashed with water and sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customdried
  6. customevaporated in a vacuum
  7. customCrystallization from ether

Sources & evidence

ORD record
ord-13b8c38744b3464bac179508fdedb168
Source dataset
uspto-grants-2001_10
Patent number
US06297266B1

Reaction notes

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