Water → tert-Butyl 2-(2-{[3-chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)ethyl carbonate

HRID 1797319ノート

反応式

HRID 1797319 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][CH2:16][OH:17])[CH:5]=[CH:4][C:3]=1[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26])=[O:19].[C:27]([O:31][C:32](ONC(C1C=CC=CC=1)C#N)=[O:33])([CH3:30])([CH3:29])[CH3:28].O.CCOC(C)=O>C(N(CC)CC)C>[C:32](=[O:33])([O:17][CH2:16][CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH:8][C:6]1[CH:5]=[CH:4][C:3]([C:18](=[O:19])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])=[C:2]([Cl:1])[CH:7]=1)[O:31][C:27]([CH3:30])([CH3:29])[CH3:28]

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10270233(2-Chloro-4-{[2-(2-hydroxyethyl)phenyl]amino}phenyl)(2-methylphenyl)methanoneHCID 13876148{[(Tert-butoxycarbonyl)oxy]amino}(phenyl)acetonitrile

生成物 1

HCID 22174529tert-Butyl 2-(2-{[3-chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)ethyl carbonate

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

反応条件

温度
70 °C

実験手順

Compound 102 (200 mg) was dissolved in dry triethylamine (3.0 mL) and {[(tert-butoxycarbonyl)oxy]amino}(phenyl)acetonitrile (148 mg) was added. The solution was stirred at 70° C. for 5 h. The reaction mixture was cooled to room temperature and then poured into a mixture of water and EtOAc. The aqueous phase was extracted with more EtOAc (×2). The combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using petroleum ether/diethyl ether 8:1 as the eluent to afford the title compound.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe aqueous phase was extracted with more EtOAc (×2)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-32f21bfe390349cf8480ba3afa2da2f8
出典データセット
uspto-grants-2006_04
特許番号
US07034015B2

反応ノート

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