4-Methylmorpholine → Acetylprolylalanylprolyl-2-azaalanyl-l-lactic acid ethyl ester

HRID 461781Notes

Reaction equation

HRID 461781 reaction equation
[C:1]([N:4]1[CH2:23][CH2:22][CH2:21][C@H:5]1[C:6]([NH:8][C@H:9]([C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([OH:17])=O)=[O:12])[CH3:10])=[O:7])(=[O:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[CH2:39]([O:41][C:42](=[O:51])[C@:43]([C:46](=[O:50])[N:47]([CH3:49])[NH2:48])([CH3:45])[OH:44])[CH3:40]>C(Cl)Cl.O1CCCC1>[CH2:39]([O:41][C:42](=[O:51])[C@:43]([C:46](=[O:50])[N:47]([CH3:49])[NH:48][C:15](=[O:17])[C@@H:14]1[CH2:18][CH2:19][CH2:20][N:13]1[C:11](=[O:12])[C@H:9]([CH3:10])[NH:8][C:6](=[O:7])[C@@H:5]1[CH2:21][CH2:22][CH2:23][N:4]1[C:1](=[O:3])[CH3:2])([CH3:45])[OH:44])[CH3:40]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 14503264AcetylprolylalanylprolineHCID 1317109772-Azaalanyl-l-lactic acid ethyl ester

Product 1

HCID 131710976Acetylprolylalanylprolyl-2-azaalanyl-l-lactic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Acetylprolylalanylproline (2 mmole) is dissolved in methylene chloride (5 ml) containing N-methylmorpholine (2 mmole) and diluted with dry tetrahydrofuran (400 ml). To this stirred solution at -20° to -25° is added isobutyl chloroformate (2 mmole) and the mixture is stirred for 15 minutes. A solution of 2-azaalanyl-l-lactic acid ethyl ester (2 mmole) in tetrahydrofuran (2 ml) is then added. The mixture is allowed to warm to room temperature over a period of 1 hour and stirred for a further 3 hours. The mixture is filtered, and the filtrate is evaporated to dryness. Chromatography on silica gel (38 gm) and elution with 5% methanol in chloroform gives acetylprolylalanylprolyl-2-azaalanyl-l-lactic acid ethyl ester.

Workup

  1. stirringstirred for a further 3 hours
  2. filtrationThe mixture is filtered
  3. customthe filtrate is evaporated to dryness
  4. washChromatography on silica gel (38 gm) and elution with 5% methanol in chloroform

Sources & evidence

ORD record
ord-fc573c933d654758865ed101236f25ba
Source dataset
uspto-grants-1977_12
Patent number
US04064236

Reaction notes

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