Acetic Acid → {4-[(2,5-Difluorobenzoyl)-hydrazono]-4-phenylbutyl}-carbamic acid tert-butyl ester

HRID 270488Notes

Reaction equation

HRID 270488 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][CH2:10][C:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[F:20][C:21]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:22]=1[C:23]([NH:25][NH2:26])=[O:24].CC(O)=O>CCO>[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][CH2:10][C:11](=[N:26][NH:25][C:23](=[O:24])[C:22]1[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:21]=1[F:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 27740742,5-DifluorobenzohydrazideHCID 14267858tert-Butyl (4-oxo-4-phenylbutyl)carbamate

Product 1

HCID 86604829{4-[(2,5-Difluorobenzoyl)-hydrazono]-4-phenylbutyl}-carbamic acid tert-butyl esterYield 101.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4-oxo-4-phenylbutyl)-carbamic acid tert-butyl ester (3.2 g, 12.2 mmol) and 2,5-difluorobenzoic acid hydrazide (2.1 g, 12 mmol) in EtOH (40 mL) was added HOAc (0.5 mL). The reaction was then heated to reflux and stirred for 3 days. The reaction mixture was then cooled to room temperature and concentrated to give desired product (5.1 g).

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6cb2c12c554a4f459c1c194c414adf85
Source dataset
uspto-grants-2008_11
Patent number
US07449486B2

Reaction notes

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