Morpholine → Z-(L)-Phe morpholin-4-ylamide

HRID 1654681Notes

Reaction equation

[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1CCC([N:29]=C=NC2CCCCC2)CC1.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1>C(Cl)Cl>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[N:38]1([NH-:29])[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4.49 g of Z-(L)-Phe-OH in 190 ml of methylene chloride is cooled to 0° C. and 3.09 g of DCC are added. After stirring for 20 minutes at 0° C., a solution of 1.31 ml of morpholine in 10 ml of methylene chloride is added dropwise thereto over a period of 15 minutes. The reaction mixture is stirred for a further 24 hours at room temperature and, after the precipitated dicyclohexylurea has been filtered off, is washed in succession with methylene chloride, aqueous sodium hydrogen carbonate solution and brine. Drying over sodium sulfate and concentration yield the crude title compound which crystallises from ether. TLC Rf (C)=0.55.

Workup

waitover a period of 15 minutes
stirringThe reaction mixture is stirred for a further 24 hours at room temperature
filtrationafter the precipitated dicyclohexylurea has been filtered off
washis washed in succession with methylene chloride, aqueous sodium hydrogen carbonate solution and brine
dry with materialDrying over sodium sulfate and concentration

Sources & evidence

ORD record: ord-71ad355629e24948b283ac1ee6ab413e
Source dataset: uspto-grants-1995_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05409927

Reaction notes

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