Acetic Anhydride → HCID 178472021, compound

HRID 2099314Notes

Reaction equation

HRID 2099314 reaction equation
[O:1]=[C:2]([C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[C:11]([O:17][CH3:18])[C:10]=1[F:19])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:20](OC(=O)C)(=O)C.C(OCC)(OCC)OCC.[F:37][C:38]([F:42])([F:41])[CH2:39][NH2:40]>>[F:37][C:38]([F:42])([F:41])[CH2:39][NH:40][CH:20]=[C:3]([C:2](=[O:1])[C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[C:11]([O:17][CH3:18])[C:10]=1[F:19])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 31214Ethyl orthoformateHCID 10588473Ethyl 3-oxo-3-(2,4,5-trifluoro-3-methoxyphenyl)propanoate

Product 1

HCID 178472021HCID 178472021, compound

Procedure

2.00 g (5.79 mmol) of ethyl 3-oxo-3-(2,4,5-trifluoro-3-methoxyphenyl)propanoate (for preparation see Journal of Medicinal Chemistry (1995), 38 (22), 4478-87) are stirred under reflux in 3.8 ml (4.14 g, 40.55 mmol) of acetic anhydride and 4.82 ml (4.29 g, 28.96 mmol) of triethyl orthoformate for 2 h. The solvent is subsequently removed completely on a rotary evaporator and the residue is dissolved in 10 ml of ethanol. 1.03 g (10.43 mmol) of 2,2,2-trifluoro-1-aminoethane are added dropwise to the ice-cooled solution, and the mixture is brought to room temperature and stirred at that temperature overnight. For the work-up, the solvent is removed and the residue is reacted further as a crude product without purification steps.

Workup

  1. customThe solvent is subsequently removed completely on a rotary evaporator
  2. dissolutionthe residue is dissolved in 10 ml of ethanol
  3. temperaturecooled solution
  4. customis brought to room temperature
  5. customFor the work-up, the solvent is removed
  6. customthe residue is reacted further as a crude product without purification steps

Sources & evidence

ORD record
ord-4d461b049c904621a3e81ecb18ed90b1
Source dataset
uspto-grants-2009_08
Patent number
US07569563B2

Reaction notes

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