Ethanol → N-(4-benzyloxycarbonylaminophenyl)-4-methyl-3-oxo-2-[1-phenyl-2-(4-fluorophenyl)-2-oxoethyl]pentanamide

HRID 277566Notes

Reaction equation

HRID 277566 reaction equation
[CH3:1][CH:2]([CH3:16])[C:3](=[O:15])[C:4](=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:5]([NH2:7])=[O:6].[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1.C([N:28]([CH2:31]C)[CH2:29][CH3:30])C.[OH2:33].[CH3:34][CH2:35][OH:36]>[Br-].C([N+]1C(C)=C(CCO)SC=1)C>[CH2:35]([O:36][C:31]([NH:28][C:29]1[CH:30]=[CH:11][C:10]([NH:7][C:5](=[O:6])[CH:4]([CH:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:22]([C:21]2[CH:24]=[CH:25][C:18]([F:17])=[CH:19][CH:20]=2)=[O:23])[C:3](=[O:15])[CH:2]([CH3:16])[CH3:1])=[CH:9][CH:8]=1)=[O:33])[C:34]1[CH:5]=[CH:4][CH:3]=[CH:2][CH:1]=1

Participants

7

Reactant 5

HCID 702EthanolHCID 962WaterHCID 8471TriethylamineHCID 680234-FluorobenzaldehydeHCID 867578684-Methyl-3-oxo-2-(phenylmethylene)pentanamide

Product 1

HCID 18314607N-(4-benzyloxycarbonylaminophenyl)-4-methyl-3-oxo-2-[1-phenyl-2-(4-fluorophenyl)-2-oxoethyl]pentanamide

Reagents, catalysts & solvents 1

HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromideCatalyst

Procedure

Step B—N-(4-benzyloxycarbonylamino)phenyl)-4-methyl-3-oxo-2-(phenylmethylene)pentanamide (10 mmol), 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (3 mmol), 4-fluorobenzaldehyde (10 mmol) and triethylamine (10 mmol) are heated at reflux in EtOH (150 mL). The progress of the reaction is monitored by tlc. When the reaction is complete, the mixture is cooled and added to water. The aqueous solution is extracted with EtOAc, and the extract is dried and evaporated. The residue is chromatographed to afford the product N-(4-benzyloxycarbonylaminophenyl)-4-methyl-3-oxo-2-[1-phenyl-2-(4-fluorophenyl)-2-oxoethyl]pentanamide 7 (R=4-NHCbz).

Workup

  1. temperaturethe mixture is cooled
  2. extractionThe aqueous solution is extracted with EtOAc
  3. customthe extract is dried
  4. customevaporated
  5. customThe residue is chromatographed

Sources & evidence

ORD record
ord-b23dcddd3e8f4628bde981e77c4992c7
Source dataset
uspto-grants-2002_03
Patent number
US06355810B1

Reaction notes

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