Ethyl bromopyruvate → 2-Piperidine-4-yl-thiazole-4-carboxylic acid ethyl ester

HRID 507288

Reaction equation

HRID 507288 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[S:16])[NH2:15])[CH2:10][CH2:9]1)=O)(C)(C)C.Br[CH2:18][C:19](=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)C>[CH2:23]([O:22][C:20]([C:19]1[N:15]=[C:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[S:16][CH:18]=1)=[O:21])[CH3:24]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylate

Product 1

HCID 579359592-Piperidine-4-yl-thiazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 10 g (41 mmol) 4-thiocarbamoyl-piperidine-1-carboxylic acid tert-butyl ester (commercially available) and 7.98 g (41 mmol) ethyl bromopyruvate (commercially available) in 120 ml ethanol was stirred at 70° C. for 90 min. The mixture was evaporated to dryness, Na2CO3 aq. was added and the residue was extracted with ethyl acetate. The organic phases were washed with NaCl aq., dried with MgSO4 and evaporated to dryness. The residue was purified on silica eluting with DCM/MeOH/25% NH3 in water 100/20/1 to yield after evaporation of the product fractions 7.28 g (74%) of the title compound as light brown solid.

Workup

  1. customThe mixture was evaporated to dryness, Na2CO3 aq.
  2. additionwas added
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe organic phases were washed with NaCl aq.
  5. dry with materialdried with MgSO4
  6. customevaporated to dryness
  7. customThe residue was purified on silica eluting with DCM/MeOH/25% NH3 in water 100/20/1
  8. customto yield
  9. customafter evaporation of the product fractions 7.28 g (74%) of the title compound as light brown solid

Sources & evidence

ORD record
ord-0d3c725b12274cf9a1c6d1826071b2fb
Source dataset
uspto-grants-2010_08
Patent number
US07786143B2

Linked notes

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