4-Methylmorpholine → Acetylalanylalanylprolyl-2-azaalanyl-DL-lactamide

HRID 461784Notes

Reaction equation

HRID 461784 reaction equation
[C:1]([NH:4][C@H:5]([C:7]([NH:9][C@H:10]([C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=O)=[O:13])[CH3:11])=[O:8])[CH3:6])(=[O:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:37][N:38]([C:40]([C:42]([CH3:47])([OH:46])[C:43]([NH2:45])=[O:44])=[O:41])[CH3:39]>O1CCCC1>[C:1]([NH:4][C@H:5]([C:7]([NH:9][C@H:10]([C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([NH:37][N:38]([C:40]([C:42]([CH3:47])([OH:46])[C:43]([NH2:45])=[O:44])=[O:41])[CH3:39])=[O:18])=[O:13])[CH3:11])=[O:8])[CH3:6])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 12895631AcetylalanylalanylprolineHCID 1317109792-Azaalanyl-DL-lactamide

Product 1

HCID 131710981Acetylalanylalanylprolyl-2-azaalanyl-DL-lactamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Acetylalanylalanylproline (2 mmole) and N-methylmorpholine (2 mmole) are dissolved in dry tetrahydrofuran (200 ml) and cooled to -20° to -25°. Isobutyl chloroformate (2 mmole) is added, and the mixture is stirred at -20° for 10 minutes. A solution of 2-azaalanyl-dl-lactamide (2 mmole) in tetrahydrofuran (10 ml) is added dropwise, and the mixture is allowed to warm to room temperature over a period of 2 hours and stirred for a further 3 hours. The precipitate is filtered off and the filtrate is evaporated to dryness. Chromatography of the residue on silica gel (70 gm) and elution with 18% methanol in chloroform gives acetylalanylalanylprolyl-2-azaalanyl-dl-lactamide.

Workup

  1. temperaturecooled to -20° to -25°
  2. stirringstirred for a further 3 hours
  3. filtrationThe precipitate is filtered off
  4. customthe filtrate is evaporated to dryness
  5. washChromatography of the residue on silica gel (70 gm) and elution with 18% methanol in chloroform

Sources & evidence

ORD record
ord-e55175b823134fe5ace7da416d5ad15d
Source dataset
uspto-grants-1977_12
Patent number
US04064236

Reaction notes

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