Hydrochloric Acid → HCID 59499318, compound

HRID 886811Notes

Reaction equation

HRID 886811 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[N:12]=[C:13]([NH:16][C:17]([N:19]([CH2:28][CH2:29][CH:30]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[O:18])[S:14][CH:15]=2)[O:8][N:7]=1)=[O:5])C.[OH-].[Na+].Cl>CCO>[C:37]1([CH:30]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:29][CH2:28][N:19]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:17](=[O:18])[NH:16][C:13]2[S:14][CH:15]=[C:11]([C:9]3[O:8][N:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:10]=3)[N:12]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11955231HCID 11955231, compound

Product 1

HCID 59499318HCID 59499318, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

18 mg (0.03 mmoles, 1 eq) of 5-{2-[3-(3,3-diphenyl-propyl)-3-(2-morpholin-4-yl-ethyl)-ureido]-thiazol-4-yl}-isoxazole-3-carboxylic acid ethyl ester (obtained in example 30) are dissolved in 1.5 mL of EtOH then 2 eq of 1 N NaOH are added to the solution. The mixture is stirred at room temperature for 3 hours prior to neutralisation at pH 5-6 with a 2 N HCl solution. The aqueous phase is extracted with AcOEt then the organic substances collected are washed with brine, dried over MgSO4 prior to evaporation to give 5-{2-[3-(3,3-diphenyl-propyl)-3-(2-morpholin-4-yl-ethyl)-ureido]-thiazol-4-yl}-isoxazole-3-carboxylic acid (obtained in example 32) (quantitative yield) in the form of a white solid.

Workup

  1. extractionThe aqueous phase is extracted with AcOEt
  2. customthe organic substances collected
  3. washare washed with brine
  4. dry with materialdried over MgSO4
  5. customto evaporation

Sources & evidence

ORD record
ord-8f1be4552c9d4807b4f0e63534d9d10f
Source dataset
uspto-grants-2012_08
Patent number
US08247412B2

Reaction notes

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