Ethyl Acetate → HCID 54394959、化合物

HRID 1789811ノート

反応式

HRID 1789811 の反応式
[CH3:1][CH:2]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[H-].[Na+].[C:17]([O:21][C:22](=[O:32])[NH:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30]Br)=[CH:26][N:25]=1)([CH3:20])([CH3:19])[CH3:18].CCOC(C)=O>CN(C=O)C.CCCCCCC.CCOC(C)=O>[CH2:13]([O:12][C:10](=[O:11])[C:2]([CH2:30][C:27]1[CH:26]=[N:25][C:24]([NH:23][C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:32])=[CH:29][CH:28]=1)([CH3:1])[C:3]([O:5][C:6]([CH3:8])([CH3:9])[CH3:7])=[O:4])[CH3:14]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 13198666tert-Butyl ethyl methylpropanedioateHCID 23030321tert-Butyl (5-(bromomethyl)pyridin-2-yl)carbamate

生成物 1

HCID 54394959HCID 54394959、化合物収率 61.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒3 回HCID 21899848Ethylacetate heptane溶媒

実験手順

A solution of tert-butyl ethyl methylmalonate (457 mg, 2.26 mmol) in DMF (4 mL) was added dropwise to a suspension of NaH (90 mg, 2.26 mmol, 60% in oil) in DMF (4 mL). The reaction mixture was stirred for 20 min. A solution of (5-bromomethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (500 mg, 1.74 mmol) in DMF (2.5 mL) was added and the reaction was stirred for 70 min. EtOAc was added and the mixture was washed with water and brine, dried and concentrated under reduced pressure. Chromathography (Heptane/EtOAc, 3:1→1:3) gave 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-2-methyl-malonic acid tert-butyl ester ethyl ester (437 mg, 61% yield).

後処理

  1. stirringthe reaction was stirred for 70 min
  2. washthe mixture was washed with water and brine
  3. customdried
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-f8a92e98d3404dbf8bf128e5eee8b1de
出典データセット
uspto-grants-2006_07
特許番号
US07071175B1

反応ノート

読み込み中…