4-Methylmorpholine → Acetylalanylalanylprolyl-2-azaalanylalanine ethyl ester

HRID 437128Notes

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.[CH2:37]([O:39][C:40](=[O:49])[C@H:41]([CH3:48])[NH:42][C:43](=[O:47])[N:44]([CH3:46])[NH2:45])[CH3:38]>O1CCCC1>[CH2:37]([O:39][C:40](=[O:49])[C@H:41]([CH3:48])[NH:42][C:43](=[O:47])[N:44]([CH3:46])[NH:45][C:16](=[O:18])[C@@H:15]1[CH2:19][CH2:20][CH2:21][N:14]1[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])[CH3:38]

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of acetylalanylalanylproline (3 mmole) and N-methylmorpholine (3 mmole) in dry tetrahydrofuran (110 ml) at -20° to -25° C. is added isobutyl chloroformate (3 mmole) and stirred at -20° C. for 10 minutes. A solution of 2-azaalanylalanine ethyl ester (3 mmole) in tetrahydrofuran (15 ml) is added dropwise. The resulting mixture is allowed to warm to room temperature over a period of 1 hour and stirred overnight. The precipitate is filtered off and the filtrate is concentrated to dryness. Chromatography on silica gel (70 gm) and elution with 8% methanol in chloroform gives acetylalanylalanylprolyl-2-azaalanylalanine ethyl ester.

Workup

temperatureto warm to room temperature over a period of 1 hour
stirringstirred overnight
filtrationThe precipitate is filtered off
concentrationthe filtrate is concentrated to dryness
washChromatography on silica gel (70 gm) and elution with 8% methanol in chloroform

Sources & evidence

ORD record: ord-1e93e82094a54c588c10bfec846b7734
Source dataset: uspto-grants-1977_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04029772

Reaction notes

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