Ethanol → ethyl Nalpha-benzyloxycarbonyl-L-lysinate

HRID 979176

反応式

HRID 979176 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:18]([OH:20])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21](O)[CH3:22].S(=O)(=O)(O)O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 75172N-alpha-Benzyloxycarbonyl-L-lysine

生成物 1

HCID 13851264ethyl Nalpha-benzyloxycarbonyl-L-lysinate収率 91%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture containing 29.9 gm (0.017 mol) of Nα-benzyloxycarbonyl-L-lysine, 30 ml of ethanol, and 9.0 ml of concentrated sulfuric acid in 250 ml of methylene chloride was refluxed for 22.5 hours. The reaction mixture was then cooled to room temperature and basified to pH of about 13 by the careful addition of a saturated aqueous solution of potassium carbonate. The aqueous phase was removed and the organic phase was washed one more time with a saturated potassium carbonate solution. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo to give 29.8 gm (91% ) of ethyl Nα-benzyloxycarbonyl-L-lysinate (II-F) as an oil.

後処理

  1. temperaturewas refluxed for 22.5 hours
  2. customThe aqueous phase was removed
  3. washthe organic phase was washed one more time with a saturated potassium carbonate solution
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-c7dcab290ba14e1698ae447fcf7f853b
出典データセット
uspto-grants-1987_05
特許番号
US04666906

関連ノート

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