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

HRID 1866549노트

반응식

HRID 1866549 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4a8fc45bb1ab419692edecb4baa98f76
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07629358B2

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