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

HRID 1866549ノート

反応式

HRID 1866549 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4a8fc45bb1ab419692edecb4baa98f76
出典データセット
uspto-grants-2009_12
特許番号
US07629358B2

反応ノート

読み込み中…