Triethylamine → 3-[3-(2-tert-Butoxycarbonylamino-2-methyl-propyl)-phenyl]-acrylic acid benzyl ester

HRID 1866549Notes

Reaction equation

HRID 1866549 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]([CH3:18])([CH3:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Br)[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[C:20]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:23])[CH:21]=[CH2:22].P(OC1C=CC(C)=CC=1)(OC1C=CC(C)=CC=1)OC1C=CC(C)=CC=1.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:25]([O:24][C:20](=[O:23])[CH:21]=[CH:22][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:19])([CH3:18])[CH3:17])[CH:11]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 12106Phosphorous acid, tris(methylphenyl) esterHCID 75617Benzyl acrylateHCID 58907464tert-butyl N-[1-(3-bromophenyl)-2-methylpropan-2-yl]carbamate

Product 1

HCID 690235023-[3-(2-tert-Butoxycarbonylamino-2-methyl-propyl)-phenyl]-acrylic acid benzyl esterYield 90%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of [2-(3-bromophenyl)-1,1-dimethylethyl]carbamic acid tert-butyl ester (preparation 32), (2 g, 6.09 mmol), benzyl acrylate (2 g, 12.19), palladium (II) acetate (204 mg, 0.91 mmol), tri-p-tolyl phosphite (556 mg, 1.83 mmol) and triethylamine (2.12 mL, 15.22 mmol) in acetonitrile (100 mL) was heated under reflux for 48 hours. The reaction mixture was then concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with ethyl acetate:pentane to afford the title compound as a pale yellow oil in 90% yield, 2.23 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hours
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. customthe residue was purified by column chromatography on silica gel
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-4a8fc45bb1ab419692edecb4baa98f76
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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