L-Phenylalanine → Phenylalanine butyramide

HRID 2066347Notes

Reaction equation

[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.[C:13]([O:18]C(=O)CCC)(=O)[CH2:14][CH2:15][CH3:16]>>[C:13]([NH2:1])(=[O:18])[CH2:14][CH2:15][CH3:16].[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

Participants

Reactant 2

HCID 6140L-Phenylalanine

HCID 7798Butyric anhydride

Product 1

HCID 68631493Phenylalanine butyramide

Conditions

Temperature: 100 °C

Procedure

5 g of phenylalanine was added to 20 mL of butyric anhydride and the resulting mixture heated to about 100° C. for about 3 h. Excess butyric anhydride was then removed under reduced pressure to provide a solid residue that was recrystallized from ethanol to provide phenylalanine butyramide.

Workup

customExcess butyric anhydride was then removed under reduced pressure
customto provide a solid residue that
customwas recrystallized from ethanol

Sources & evidence

ORD record: ord-75a29ee0177b41b9a5c82eed28243734
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293253B2

Reaction notes

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