4-Methylmorpholine → Acetylalanylalanylleucyl-2-azaalanyl-DL-lactic acid ethyl ester

HRID 461788ノート

反応式

HRID 461788 の反応式
[C:1]([NH:4][C@H:5]([C:7]([NH:9][C@H:10]([C:12]([NH:14][C@H:15]([C:20]([OH:22])=O)[CH2:16][CH:17]([CH3:19])[CH3:18])=[O:13])[CH3:11])=[O:8])[CH3:6])(=[O:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[CH2:38]([O:40][C:41](=[O:50])[C:42]([C:45](=[O:49])[N:46]([CH3:48])[NH2:47])([CH3:44])[OH:43])[CH3:39]>C(Cl)Cl.O1CCCC1>[CH2:38]([O:40][C:41](=[O:50])[C:42]([C:45](=[O:49])[N:46]([CH3:48])[NH:47][C:20](=[O:22])[C@H:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[NH:14][C:12](=[O:13])[C@H:10]([CH3:11])[NH:9][C:7](=[O:8])[C@H:5]([CH3:6])[NH:4][C:1](=[O:3])[CH3:2])([CH3:44])[OH:43])[CH3:39]

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 54064604AcetylalanylalanylleucineHCID 1317109802-Azaalanyl-dl-lactic acid ethyl ester

生成物 1

HCID 131710982Acetylalanylalanylleucyl-2-azaalanyl-DL-lactic acid ethyl ester

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Acetylalanylalanylleucine (1.5 mmole) and N-methylmorpholine (3 mmole) are dissolved in methylene chloride (10 ml) and diluted with dry tetrahydrofuran (250 ml) and cooled to -20° to -25°. Isobutyl chloroformate (1.5 mmole) is added with stirring and the mixture is stirred for 10 minutes. A solution of 2-azaalanyl-dl-lactic acid ethyl ester (1.5 mmole, Example 5, Step A) in tetrahydrofuran (3 ml) is added and the mixture is allowed to warm to room temperature over a period of 2 hours and stirred overnight. The precipitate is filtered off and the filtrate is evaporated to dryness. Chromatography on silica gel (25 gm) and elution with 12% methanol in chloroform gives acetylalanylalanylleucyl-2-azaalanyl-dl-lactic acid ethyl ester.

後処理

  1. temperaturecooled to -20° to -25°
  2. stirringthe mixture is stirred for 10 minutes
  3. stirringstirred overnight
  4. filtrationThe precipitate is filtered off
  5. customthe filtrate is evaporated to dryness
  6. washChromatography on silica gel (25 gm) and elution with 12% methanol in chloroform

出典と根拠

ORDレコード
ord-7ce4ed708b4e47e69982573dd8c2ccc5
出典データセット
uspto-grants-1977_12
特許番号
US04064236

反応ノート

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