Ethyl Acetate → HCID 67029238, compound

HRID 244712Notes

Reaction equation

HRID 244712 reaction equation
N1CCC([CH2:7][C:8]2[S:9][CH:10]=[C:11]([C:13]([O:15]CC)=[O:14])[N:12]=2)CC1.[OH-].[Na+].C(O[CH2:24][CH3:25])(=O)C>O>[CH2:8]([N:12]([CH2:7][C:8]1[S:9][CH:10]=[C:11]([C:13]([OH:15])=[O:14])[N:12]=1)[CH2:11][CH2:24][CH3:25])[CH3:7]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 67029196HCID 67029196, compound

Product 1

HCID 67029238HCID 67029238, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethyl 2-(4-piperidinylmethyl)-1,3-thiazole-4-carboxylate (19 g, 74 mmol) was added a solution of sodium hydroxide (3.6 g, 88.8 mmol) in water (250 ml). The resulting mixture was stirred at room temperature for 18 h, then ethyl acetate was added and the layers were separated. The aqueous phase was acidified with conc. H2SO4 and concentrated to give a brown solid. The solid was recrystallised from methanol/ethyl acetate, then again from DCM/methanol to give the title compound as a light brown solid (16 g).

Workup

  1. customthe layers were separated
  2. concentrationconcentrated
  3. customto give a brown solid
  4. customThe solid was recrystallised from methanol/ethyl acetate

Sources & evidence

ORD record
ord-30c545042399470cb6afd7234ee3978e
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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