Sodium Hydroxide → HCID 59174089, compound

HRID 646407Notes

Reaction equation

HRID 646407 reaction equation
C([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[C:14]([C:16]([NH:19][C:20](=[O:22])[CH3:21])([CH3:18])[CH3:17])[N:15]=2)=[CH:7][CH:6]=1)C.[OH-].[Na+]>O1CCCC1.C(O)C>[C:20]([NH:19][C:16]([C:14]1[N:15]=[C:11]([C:8]2[CH:7]=[CH:6][C:5]([C:4]([OH:23])=[O:3])=[CH:10][CH:9]=2)[S:12][CH:13]=1)([CH3:18])[CH3:17])(=[O:22])[CH3:21]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59264697HCID 59264697, compound

Product 1

HCID 59174089HCID 59174089, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-[4-(1-Acetylamino-1-methyl-ethyl)-thiazol-2-yl]-benzoic acid ethyl ester (0.13 g, 0.39 mmol) is dissolved in 2 mL tetrahydrofuran and 2 mL ethanol. 2N sodium hydroxide (1.17 mmol, 0.587 mL) is added and the mixture is heated to reflux for 1 hour. The reaction is concentrated to dryness and the resulting residue is dissolved in 95:5 dichloromethane/isopropanol layered with 0.1N HCl. The organics are separated and dried over sodium sulfate, filtered, and concentrated to give 0.106 g of the pure titled compound. MS (m/e) 303.2 (M−H)−

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 1 hour
  3. concentrationThe reaction is concentrated to dryness
  4. dissolutionthe resulting residue is dissolved in 95:5 dichloromethane/isopropanol
  5. customThe organics are separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e8a167bd93e447f5a82ec9e1117bf4c9
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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