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

HRID 1654682Notes

Reaction equation

HRID 1654682 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[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.[N:23]1([NH-:29])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.[H][H]>CO.[Pd]>[NH2:1][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.[N:23]1([NH-:29])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Participants

5

Reactant 2

HCID 131718979Z-(L)-Phe morpholin-4-ylamideHCID 178418361HCID 178418361, compound

Product 1

HCID 131718980H-(L)-Phe morpholin-4-ylamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5.5 g of Z-(L)-Phe-morpholin-4-ylamide in 150 ml of methanol is converted into the title compound by hydrogenolysis with the calculated amount of hydrogen for 1 hour at room temperature in the presence of 1.5 g of 10% Pd/C. The catalyst is filtered off and the reaction mixture is concentrated, and after dilution with ethyl acetate the resulting solution is washed with a saturated sodium hydrogen carbonate solution, dried over sodium sulfate and concentrated under reduced pressure. After column chromatography (analogously to Example 1 g)) the title compound is obtained in pure form. TLC Rf (D)=0.3.

Sources & evidence

ORD record
ord-11127a551dc74679affdeaea1f266423
Source dataset
uspto-grants-1995_04
Patent number
US05409927

Reaction notes

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