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

HRID 461788Notes

Reaction equation

HRID 461788 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7ce4ed708b4e47e69982573dd8c2ccc5
Source dataset
uspto-grants-1977_12
Patent number
US04064236

Reaction notes

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