Hydrochloric Acid → 2-Propyl-2-(3-thiazol-2-ylureido)pentanoic acid

HRID 612394Notes

Reaction equation

HRID 612394 reaction equation
C([O:3][C:4](=[O:21])[C:5]([CH2:18][CH2:19][CH3:20])([NH:9][C:10]([NH:12][C:13]1[S:14][CH:15]=[CH:16][N:17]=1)=[O:11])[CH2:6][CH2:7][CH3:8])C.Cl>[OH-].[Na+]>[CH2:6]([C:5]([NH:9][C:10]([NH:12][C:13]1[S:14][CH:15]=[CH:16][N:17]=1)=[O:11])([CH2:18][CH2:19][CH3:20])[C:4]([OH:21])=[O:3])[CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 110669732-Propyl-2-(3-thiazol-2-ylureido)pentanoic acid ethyl ester

Product 1

HCID 110873642-Propyl-2-(3-thiazol-2-ylureido)pentanoic acidYield 93%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

10.03 g of the product from stage 4 were dissolved with stirring in 200 ml of semi-concentrated sodium hydroxide solution at a temperature of 20° C. The pH was then adjusted to 4 with concentrated hydrochloric acid and extracted three times with 50 ml portions of dichloromethane. The extracts were washed once with a saturated sodium chloride solution and dried over sodium sulphate. Once the solvent had been removed by distillation, 8.48 g of 2-propyl-2-(3-thiazol-2-ylureido)pentanoic acid (93% of th.) were obtained in the form of white crystals (mp 154-155° C.).

Workup

  1. extractionextracted three times with 50 ml portions of dichloromethane
  2. washThe extracts were washed once with a saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. customOnce the solvent had been removed by distillation

Sources & evidence

ORD record
ord-a0f71aee8cec4cabb861d57f0ea9f4aa
Source dataset
uspto-grants-1999_12
Patent number
US06004963

Reaction notes

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