Ethyl Acetate → benzyl N-(3-acetyl-4-fluorophenyl)carbamate

HRID 527945Notes

Reaction equation

HRID 527945 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([F:22])=[C:17]([C:19](=[O:21])[CH3:20])[CH:18]=1.CCOC(C)=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:5]([O:4][C:2](=[O:3])[NH:12][C:13]1[CH:14]=[CH:15][C:16]([F:22])=[C:17]([C:19](=[O:21])[CH3:20])[CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 27811251-(5-Amino-2-fluorophenyl)ethanone

Product 1

HCID 68293774benzyl N-(3-acetyl-4-fluorophenyl)carbamateYield 84%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

Benzyl chloroformate (3 mL, 21.5 mmol) was added to a mixture of 1-(5-amino-2-fluorophenyl)ethanone (3 g, 19.6 mmol) and tetrabutylammonium bromide at room temperature. The reaction was stirred at room temperature for 24 hours, the crude was treated with AcOEt (50 mL) and H2O (50 mL), the organic phase was separated and evaporated in vacuo. The crude was purified by column chromatography (silica gel; MeOH/DCM). The desired fractions were collected and the solvents evaporated in vacuo to afford intermediate A40 as a cream solid (4.7 g, 84%). LCMS: 286 [M−H]−; Rt: 2.81 min (method 3).

Workup

  1. customthe organic phase was separated
  2. customevaporated in vacuo
  3. customThe crude was purified by column chromatography (silica gel; MeOH/DCM)
  4. customThe desired fractions were collected
  5. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-fca8a0adecac4c6c867330746dc475c2
Source dataset
uspto-grants-2016_05
Patent number
US09346811B2

Reaction notes

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