4-Toluenesulfonyl chloride → N-(p-toluenesulphonyl)-L-alanyl-L-proline anilide

HRID 1448734ノート

反応式

HRID 1448734 の反応式
Br.[NH2:2][C@H:3]([C:5]([N:7]1[CH2:20][CH2:19][CH2:18][C@H:8]1[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10])=[O:6])[CH3:4].[OH-].[Na+].[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>ClCCl>[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29]([NH:2][C@H:3]([C:5]([N:7]2[CH2:20][CH2:19][CH2:18][C@H:8]2[C:9]([NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:10])=[O:6])[CH3:4])(=[O:31])=[O:30])=[CH:25][CH:24]=1

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 22809936L-alanyl-L-proline anilide hydrobromide

生成物 1

HCID 40223683N-(p-toluenesulphonyl)-L-alanyl-L-proline anilide収率 93.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

1.71 g (0.005 mol) of L-alanyl-L-proline anilide hydrobromide were suspended in 20 ml of dichloromethane. To the suspension were added 22 ml of 0.5-N sodium hydroxide solution followed by 1.05 g (1.1 equivalents) of p-toluenesulphonyl chloride. The mixture was stirred vigorously for 90 minutes. 50 ml of dichloromethane were added, the organic layer was separated, washed with 50 ml of brine, dried over magnesium sulphate and evaporated to an oil which crystallised upon the addition of petroleum ether. The solid was filtered off, washed with petroleum ether and dried to yield 1.94 g (93%) of N-(p-toluenesulphonyl)-L-alanyl-L-proline anilide of melting point 145°-147° C.; [α]D20 =-126.2° (c=1.00% in glacial acetic acid).

後処理

  1. customthe organic layer was separated
  2. washwashed with 50 ml of brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated to an oil which
  5. customcrystallised upon the addition of petroleum ether
  6. filtrationThe solid was filtered off
  7. washwashed with petroleum ether
  8. customdried

出典と根拠

ORDレコード
ord-2137aa1edc914379a9f196c71edde885
出典データセット
uspto-grants-1980_02
特許番号
US04187216

反応ノート

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