Sodium Hydroxide → HCID 22315271, compound

HRID 430143Notes

Reaction equation

HRID 430143 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12](=[O:28])[CH:13]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)[CH2:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[N:8][CH:7]=1)=[O:5])C.[OH-].[Na+]>C(O)C>[CH:15]1([CH2:14][CH:13]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)[C:12]([NH:11][C:9]2[S:10][C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]=2)=[O:28])[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 46221597HCID 46221597, compound

Product 1

HCID 22315271HCID 22315271, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-[3-cyclopentyl-2-(3,4-dichlorophenyl)-propionylamino]-thiazole-5-carboxylic acid ethyl ester (prepared in Example 1(B)(g), 1.0 g, 2.27 mmol) in absolute ethanol (10 mL) was treated with a 1 N aqueous sodium hydroxide solution (4.77 mL, 4.77 mmol). The reaction mixture was heated under reflux for 15 h. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo to remove absolute ethanol. The resulting yellow residue was acidified to pH=2 with concentrated hydrochloric acid and extracted with ethyl acetate (2×75 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Recrystallization from ethyl acetate afforded 2-[3-cyclopentyl-2-(3,4-dichlorophenyl)-propionylamino]-thiazole-5-carboxylic acid (210 mg, 22%) as a white solid: mp 269-270° C.; FAB-HRMS m/e calcd for C18H18Cl2N2O3S (M+H)+ 413.0493, found 413.0483.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 15 h
  3. concentrationconcentrated in vacuo
  4. customto remove absolute ethanol
  5. extractionextracted with ethyl acetate (2×75 mL)
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-66ed2cbd6f424dc6999d9e0f066b1fc7
Source dataset
uspto-grants-2001_11
Patent number
US06320050B1

Reaction notes

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