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

HRID 461788

반응식

HRID 461788 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7ce4ed708b4e47e69982573dd8c2ccc5
출처 데이터셋
uspto-grants-1977_12
특허 번호
US04064236

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