Potassium Carbonate → HCID 178470562, compound

HRID 493712

Reaction equation

HRID 493712 reaction equation
Br[CH2:2][C:3]1[N:4]([CH3:15])/[C:5](=[N:13]/[CH3:14])/[S:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[NH2:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:11]([O:10][C:8]([C:7]1[S:6]/[C:5](=[N:13]\[CH3:14])/[N:4]([CH3:15])[C:3]=1[CH2:2][NH:16][CH:17]1[CH2:18][CH2:19][N:20]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:21][CH2:22]1)=[O:9])[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 178466404-Amino-1-N-Cbz-piperidineHCID 178470561HCID 178470561, compound

Product 1

HCID 178470562HCID 178470562, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl (2Z)-4-bromomethyl-3-methyl-2-methylimino-2,3-dihydro-1,3-thiazole-5-carboxylate (3.0 g) obtained in Example 13) as a synthetic intermediate and benzyl 4-aminopiperidine-1-carboxylate (3.3 g) were dissolved in DMF (50 mL). Potassium carbonate (3.8 g) was added thereto, and the mixture was mixed at 70° C. for 4 hours. The solvent was distilled off, and the residue was poured into water. The mixture was then extracted with a mixed solution of chloroform-methanol, and the extract was dried over anhydrous magnesium sulfate. The solvent-was distilled off, and the residue was purified with a silica gel column to give the title compound (3.1 g) as pale yellow crystals.

Workup

  1. additionthe mixture was mixed at 70° C. for 4 hours
  2. distillationThe solvent was distilled off
  3. additionthe residue was poured into water
  4. extractionThe mixture was then extracted with a mixed solution of chloroform-methanol
  5. dry with materialthe extract was dried over anhydrous magnesium sulfate
  6. distillationThe solvent-was distilled off
  7. customthe residue was purified with a silica gel column

Sources & evidence

ORD record
ord-6a6f7863f7d446ddb52a33181cfdc2a6
Source dataset
uspto-grants-2009_05
Patent number
US07534887B2

Linked notes

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