Potassium Carbonate → 2-[3-(Benzyloxycarbonylamino-methyl)-piperidin-1-yl]-thiazole-4-carboxylic acid ethyl ester

HRID 460210Notes

Reaction equation

HRID 460210 reaction equation
[CH2:1]([O:8][C:9](=[O:18])[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:25]([O:27][C:28]([C:30]1[N:31]=[C:32](Br)[S:33][CH:34]=1)=[O:29])[CH3:26]>CC#N>[CH2:25]([O:27][C:28]([C:30]1[N:31]=[C:32]([N:14]2[CH2:15][CH2:16][CH2:17][CH:12]([CH2:11][NH:10][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:18])[CH2:13]2)[S:33][CH:34]=1)=[O:29])[CH3:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 353965Ethyl 2-bromo-1,3-thiazole-4-carboxylateHCID 21104689Piperidin-3-ylmethyl-carbamic acid benzyl ester

Product 1

HCID 694109422-[3-(Benzyloxycarbonylamino-methyl)-piperidin-1-yl]-thiazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of piperidin-3-ylmethyl-carbamic acid benzyl ester (43 mg, 0.17 mmol) in CH3CN (5 mL), at RT under N2, K2CO3 (26 mg, 0.19 mmol) and 2-bromo-thiazole-4-carboxylic acid ethyl ester (41 mg, 0.17 mmol) were added. The resulting mixture was heated at reflux for 29 h. The solvent was evaporated in vacuo. The residue was treated with a saturated solution of NH4Cl (aq) (10 mL) and extracted with EtOAc (10 mL). The organic layer was separated, dried over Na2SO4, filtered and the solvent evaporated in vacuo. The residue was purified by flash chromatography on silica gel (1:2, EtOAc:hexane) to yield the title compound as a colorless oil. MS m/z: 404.2 (M+H). Calc'd. for C20H25N3O4S-403.50.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 29 h
  3. customThe solvent was evaporated in vacuo
  4. additionThe residue was treated with a saturated solution of NH4Cl (aq) (10 mL)
  5. extractionextracted with EtOAc (10 mL)
  6. customThe organic layer was separated
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customthe solvent evaporated in vacuo
  10. customThe residue was purified by flash chromatography on silica gel (1:2, EtOAc:hexane)

Sources & evidence

ORD record
ord-c53d3e810b5e4b51b0b8b3464572d4d4
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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