Benzoyl chloride → N-benzoyl-L-alanyl-L-proline ethylamide

HRID 47045ノート

反応式

HRID 47045 の反応式
Br.[CH2:2]([NH:4][C:5](=[O:16])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:15])[C@H:12]([CH3:14])[NH2:13])[CH3:3].[OH-].[Na+].[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[CH2:2]([NH:4][C:5](=[O:16])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:15])[C@H:12]([CH3:14])[NH:13][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:3]

参加物

5

反応物 3

HCID 7412Benzoyl chlorideHCID 14798Sodium Hydroxide2 回HCID 70602162L-alanyl-L-proline ethylamide hydrobromide

生成物 1

HCID 54309979N-benzoyl-L-alanyl-L-proline ethylamide収率 68.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1.42 g (0.0048 mol) of L-alanyl-L-proline ethylamide hydrobromide were dissolved in 20 ml of methylene chloride, 21.8 ml (0.01 mol) of 0.5-N sodium hydroxide solution were added followed by 0.54 ml (0.0053 mol) of benzoyl chloride. The mixture was stirred vigorously at room temperature for 1 hour with care being taken that the solution remained basic, this being achieved by the addition of a few drops of 0.5-N sodium hydroxide solution. The layers were then allowed to separate and the methylene chloride layer was separated, dried over magnesium sulphate and evaporated to an oil which crystallised on treatment with ethyl acetate. The crystals were filtered off, washed and dried to yield 1.05 g of N-benzoyl-L-alanyl-L-proline ethylamide of melting point 200°-202° C.; [α]D20 =-82.7° (c=0.99 in methanol).

後処理

  1. customto separate
  2. customthe methylene chloride layer was separated
  3. dry with materialdried over magnesium sulphate
  4. customevaporated to an oil which
  5. customcrystallised on treatment with ethyl acetate
  6. filtrationThe crystals were filtered off
  7. washwashed
  8. customdried

出典と根拠

ORDレコード
ord-00cb2a1f19a44f2d8f439eb07dc5a70f
出典データセット
uspto-grants-1979_11
特許番号
US04176116

反応ノート

読み込み中…