Trifluoroacetic acid → HCID 86626087, compound

HRID 390627Notes

Reaction equation

HRID 390627 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[C:10](/[CH:12]=[C:13](\[CH3:19])/[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:9]=[CH:8][C:7]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][NH:27][CH2:28]C(OC(C)(C)C)=O)[CH:21]=1)[CH2:2][CH2:3][CH3:4].[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39]>ClCCl>[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39].[CH2:1]([O:5][C:6]1[CH:11]=[C:10](/[CH:12]=[C:13](\[CH3:19])/[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:9]=[CH:8][C:7]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][NH:27][CH3:28])[CH:21]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86626085HCID 86626085, compound

Product 1

HCID 86626087HCID 86626087, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

g (2.2 mmol) of ethyl (E)-3-{2-butoxy-3′-[(tert-butoxycarbonylmethylamino)methyl]biphenyl-4-yl}-2-methylacrylate in 10 mL of dichloromethane and 1.5 mL of trifluoroacetic acid are stirred at room temperature for 2 hours 30 minutes. The reaction medium is evaporated to dryness and purified by chromatography on a column of silica eluted with a 98/2 and then 95/5 mixture of ethyl acetate and methanol. 1.1 g (84%) of ethyl (E)-3-(2-butoxy-3′-methylaminomethylbiphenyl-4-yl)-2-methylacrylate trifluoroacetate are obtained in the form of an orange oil.

Workup

  1. customThe reaction medium is evaporated to dryness
  2. custompurified by chromatography on a column of silica
  3. washeluted with a 98/2
  4. addition95/5 mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-7384008472cb4bdbb932ccf1222435ff
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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