Triethylamine → HCID 87529066, compound

HRID 1162365Notes

Reaction equation

HRID 1162365 reaction equation
[NH:1]=[C:2]1[N:6]([CH2:7][CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:4][S:3]1.C(N(CC)CC)C.Cl[C:29]([O:31][CH2:32][CH:33]=[CH2:34])=[O:30]>ClCCl.C(OCC)(=O)C.O>[CH2:32]([O:31][C:29](/[N:1]=[C:2]1\[S:3][CH:4]=[CH:5][N:6]\1[CH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]1)=[O:30])[CH:33]=[CH2:34]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 18052Allyl chloroformateHCID 23138404HCID 23138404, compound

Product 1

HCID 87529066HCID 87529066, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-((2-imino-1,3-thiazol-3(2H)-yl)methyl)-1-piperidinecarboxylate (0.9 g) obtained in Example 139a) and triethylamine (0.93 ml) in dichloromethane (10 ml) was added allyl chloroformate (0.35 ml) under ice-cooling, and mixed at 0° C. for 12 hours. Ice chips were added to the reaction mixture to stop the reaction, and diluted with ethyl acetate and water. The organic layer was collected by separation, washed with saturated sodium bicarbonate water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as a colorless solid (1.1 g, 96%).

Workup

  1. temperaturecooling
  2. additionmixed at 0° C. for 12 hours
  3. additionIce chips were added to the reaction mixture
  4. customthe reaction
  5. customThe organic layer was collected by separation
  6. washwashed with saturated sodium bicarbonate water and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ed384ba6ee154edfa52848963d7875fa
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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