Ethyl Acetate → HCID 22351209, compound

HRID 1278708Notes

Reaction equation

HRID 1278708 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[CH2:15]([O:22][C:23]([NH:25][CH:26]([CH:34]1[O:36][CH2:35]1)[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CCOC(C)=O>CN(C=O)C>[CH2:15]([O:22][C:23]([NH:25][CH:26]([CH:34]([OH:36])[CH2:35][N:12]1[CH2:11][CH2:10][CH:9]([CH2:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:14][CH2:13]1)[CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:24])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 36998414-(4-Fluoro-benzyl)-piperidineHCID 148872432-Benzyloxycarbonylamino-1-phenyl-3,4-epoxy-butane

Product 1

HCID 22351209HCID 22351209, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(4-fluorophenyl)methyl-piperidine (0.515 g, 2.314 mmoles) and 2-benzyloxycarbonylamino-1-phenyl-3,4-epoxy-butane (0.688 g, 2.314 mmoles) in 5 mL of DMF was stirred for 4 hours at 100° C. and cooled to room temperature. After addition of EtOAc (30 mL), the mixture was washed with water (2×) and brine. The oranic solution was dried over Na2SO4, and evaporated to give an oily residue. It was then purified by passing through a plug of silica gel with elution by EtOAc to give pure product.

Workup

  1. washthe mixture was washed with water (2×) and brine
  2. dry with materialThe oranic solution was dried over Na2SO4
  3. customevaporated
  4. customto give an oily residue
  5. customIt was then purified
  6. washwith elution by EtOAc
  7. customto give pure product

Sources & evidence

ORD record
ord-82dd88d98e7f451c898f8a2b0d2cfc41
Source dataset
uspto-grants-2002_09
Patent number
US06444686B1

Reaction notes

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