Methyl Acrylate → N-(Methoxycarbonyl)ethyl-L-leucyl-L-phenylalanine N-methylamide

HRID 1872492Notes

Reaction equation

[CH3:1][NH:2][C:3](=[O:21])[C@H:4]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH:5][C:6](=[O:13])[C@H:7]([CH2:9][CH:10]([CH3:12])[CH3:11])[NH2:8].[C:22]([O:26][CH3:27])(=[O:25])[CH:23]=[CH2:24]>C(O)C>[CH3:1][NH:2][C:3](=[O:21])[C@H:4]([CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[NH:5][C:6](=[O:13])[C@H:7]([CH2:9][CH:10]([CH3:12])[CH3:11])[NH:8][CH2:24][CH2:23][C:22]([O:26][CH3:27])=[O:25]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of L-leucyl-L-phenylalanine N-methylamide (1.09 g) in ethanol (20 ml) was treated with methyl acrylate (0.33 ml). The resulting colourless solution was heated to 70° C. over 7.5 h. The crude product was purified by flash silica chromatography, eluting with ethyl acetate/methanol (9:1) to provide the title compound was isolated as a white solid (0.482 g).

Workup

customThe crude product was purified by flash silica chromatography
washeluting with ethyl acetate/methanol (9:1)

Sources & evidence

ORD record: ord-06a15c2cc42e4db7b44d52cbf27c13db
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06110896

Reaction notes

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