4-tert-Butylcyclohexyl chloroformate → HCID 21365027、化合物

HRID 987296ノート

反応式

HRID 987296 の反応式
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C@H:19]([O:23][CH2:24][CH3:25])[C:20]([OH:22])=[O:21])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.C(=O)([O-])O.[Na+].Cl[C:32]([O:34][CH:35]1[CH2:40][CH2:39][CH:38]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH2:37][CH2:36]1)=[O:33].CO.ClCCl>O1CCCC1>[CH2:24]([O:23][C@@H:19]([CH2:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([NH:2][C:32]([O:34][CH:35]3[CH2:40][CH2:39][CH:38]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH2:37][CH2:36]3)=[O:33])=[CH:8][CH:7]=2)=[CH:13][CH:14]=1)[C:20]([OH:22])=[O:21])[CH3:25]

参加物

6

反応物 4

HCID 1706084-tert-Butylcyclohexyl chloroformate2 回HCID 516892Sodium BicarbonateHCID 21226129Dichloromethane methanolHCID 86595065HCID 86595065、化合物

生成物 1

HCID 21365027HCID 21365027、化合物収率 100%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3-{4-[2-(4-Aminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid hydro chloride (0.2 g, 0.547 mmole) and sodium hydrogen carbonate (0.05 g, 0.595 mmole) were mixed in tetrahydrofurane (5 ml), stirred at room temperature for 20 minutes and then 4-tert-butylcyclohexyl chloroformate (0.131 g, 0.599 mmole) was added. The reaction mixture was stirred at room temperature overnight and then a little more 4-tert-butylcyclohexyl chloroformate was added since the reaction was not complete according to HPLC. The reaction mixture was stirred for 2 more hours and then evaporated to dryness. Ethyl acetate and water were added to the residue and the phases were separated. The organic phase was dried with magnesium sulfate and the solvent was evaporated. Chromatography on silica gel (Isolute, SI ) using dichloromethane:heptane (1:1), followed by dichloromethane, and then methanol: dichloromethane (1:99) as eluants gave 0.28 g (93% yield) (S)-2-ethoxy-3[4-(2-[4-([{4-(tert-butyl)cyclohexyl}oxy]carbonylamino)phenyl]ethoxy)phenyl]propanoic acid.

後処理

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. stirringThe reaction mixture was stirred for 2 more hours
  3. customevaporated to dryness
  4. additionEthyl acetate and water were added to the residue
  5. customthe phases were separated
  6. dry with materialThe organic phase was dried with magnesium sulfate
  7. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-70b93e59508a49c4b9a96e87416f5c57
出典データセット
uspto-grants-2003_10
特許番号
US06630600B1

反応ノート

読み込み中…