4-Methylmorpholine → Z-Gly-Phe-Leu-OBut

HRID 905093Notes

Reaction equation

[NH:1]([C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[CH2:2][C:3]([OH:5])=O.CN1CCOCC1.ClC(OCC)=O.[NH2:29][C@H:30]([C:38]([NH:40][C@H:41]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:42][CH:43]([CH3:45])[CH3:44])=[O:39])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)C>[NH:1]([C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[CH2:2][C:3]([NH:29][C@H:30]([C:38]([NH:40][C@H:41]([C:46]([O:48][C:49]([CH3:51])([CH3:50])[CH3:52])=[O:47])[CH2:42][CH:43]([CH3:45])[CH3:44])=[O:39])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:5]

Participants

Conditions

Temperature: -10 °C

Procedure

Z-Gly-OH (25.2 g., 132 mM) was dissolved in DMF (300 ml.) and the solution was cooled to -10° C. N-methylmorpholine (14.8 ml., 132 mM) was added, followed by ethyl chloroformate (12.1 ml., 126 mM). After 3 minutes at -10° C., a solution of H-Phe-Leu-OBut (40.1 g., 120 mM) in DMF (100 ml.) was added, and the mixture was stirred at 0° C. overnight. The solvent was evaporated and the residue was dissolved in ethyl acetate (600 ml.) and washed successively with water (2×60 ml.), 2 N-aqueous potassium bicarbonate (3×60 ml.), and water (3×60 ml.). The solution was dried (MgSO4) and filtered. The solvent was evaporated to give Z-Gly-Phe-Leu-OBut.

Workup

customThe solvent was evaporated
dissolutionthe residue was dissolved in ethyl acetate (600 ml.)
washwashed successively with water (2×60 ml.), 2 N-aqueous potassium bicarbonate (3×60 ml.), and water (3×60 ml.)
dry with materialThe solution was dried (MgSO4)
filtrationfiltered
customThe solvent was evaporated

Sources & evidence

ORD record: ord-1300a3cba3a446178e7d5d7c09593040
Source dataset: uspto-grants-1983_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04421744

Reaction notes

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