Acetic Acid → HCID 21697716, compound

HRID 378999Notes

Reaction equation

HRID 378999 reaction equation
[CH2:1]([NH:8][C:9](=[O:41])[NH:10][C:11]1[S:12][CH:13]=[C:14]([C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([O:34][CH2:35][C:36]([O:38]CC)=[O:37])=[C:23]([CH:33]=2)[C:24]([O:26]CC(OCC)=O)=[O:25])=[O:17])[N:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[OH-].[Na+].C(O)(=O)C>O>[CH2:1]([NH:8][C:9](=[O:41])[NH:10][C:11]1[S:12][CH:13]=[C:14]([C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([O:34][CH2:35][C:36]([OH:38])=[O:37])=[C:23]([CH:33]=2)[C:24]([OH:26])=[O:25])=[O:17])[N:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 21697698HCID 21697698, compound

Product 1

HCID 21697716HCID 21697716, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

378 mg of ethoxycarbonylmethyl 5-{[2-(3-benzyl-ureido)-thiazole-4-carbonyl]-amino}-2-ethoxycarbonylmethoxy-benzoate, 6.5 ml of ethanol and 1.29 ml of 2N sodium hydroxide solution are stirred for 5 hrs. at RT. After the addition of 3 ml of acetic acid and 2 ml of water the mixture is warmed until a homogeneous solution is obtained. After cooling the precipitate is filtered off under suction, washed with acetic acid-water 1:1 and dried. There are obtained 290 mg of 5-{[2-(3-benzyl-ureido)-thiazole-4-carbonyl]-amino}-2-carboxymethoxy-benzoic acid, m.p. 219° C., MS: 471 (M+H)+.

Workup

  1. customat RT
  2. temperatureis warmed until a homogeneous solution
  3. customis obtained
  4. temperatureAfter cooling the precipitate
  5. filtrationis filtered off under suction
  6. washwashed with acetic acid-water 1:1
  7. customdried

Sources & evidence

ORD record
ord-66ab3fdcb63846718fb12741eeb6ea85
Source dataset
uspto-grants-2001_10
Patent number
US06297266B1

Reaction notes

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