Potassium Hydroxide → HCID 86760124, compound

HRID 1789931Notes

Reaction equation

HRID 1789931 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH:5]([CH2:11][C:12]1[S:16][C:15]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[N:14][CH:13]=1)[C:6]([O:8]CC)=[O:7])[CH3:2].[OH-].[K+]>C(O)C.C1COCC1>[CH2:1]([O:3][C:4](=[O:25])[CH:5]([CH2:11][C:12]1[S:16][C:15]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[N:14][CH:13]=1)[C:6]([OH:8])=[O:7])[CH3:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 54554701HCID 54554701, compound

Product 1

HCID 86760124HCID 86760124, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2-(2-tert-Butoxycarbonylamino-thiazol-5-ylmethyl)-malonic acid diethyl ester (158 mg; 0.43 mmol) was dissolved in ethanol (1 mL) and THF (0.5 mL), and a solution of KOH (24 mg; 0.43 mmol) in ethanol (0.14 mL) was added at 0° C. The reaction mixture was stirred at room temperature for 96 hours, and then poured onto ice-water. The aqueous phase was extracted with diethyl ether, acidified to pH 3 by addition of 0.5 M HCl, and extracted with diethyl ether. The combined organic phases were dried and concentrated to yield 2-(2-tert-butoxycarbonylamino-thiazol-5-ylmethyl)-malonic acid monoethyl ester (97 mg, 66.4%).

Workup

  1. additionpoured onto ice-water
  2. extractionThe aqueous phase was extracted with diethyl ether
  3. additionacidified to pH 3 by addition of 0.5 M HCl
  4. extractionextracted with diethyl ether
  5. customThe combined organic phases were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-26c4cbffa7844871ab7a014911a09649
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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