Cinnamyloxybenzene → (E)-N-Benzyl-N-(3-phenyl-2-propenyl)-3-phenylalanine ethyl ester

HRID 1627956Notes

Reaction equation

HRID 1627956 reaction equation
[CH2:1](OC1C=CC=CC=1)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:17]([NH:24][CH:25]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:29]([O:28][C:26](=[O:27])[C@H:25]([CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[N:24]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:1]/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:30]

Participants

3

Reactant 2

HCID 258010CinnamyloxybenzeneHCID 60991331Ethyl 2-(benzylamino)-3-phenylpropanoate

Product 1

HCID 67215712(E)-N-Benzyl-N-(3-phenyl-2-propenyl)-3-phenylalanine ethyl esterYield 95.1%

Procedure

Following the general procedure using cinnamyloxybenzene (105 mg, 0.50 mmol) and ethyl 2-(benzylamino)-3-phenylpropanoate (212 mg, 0.75 mmol), the reaction was stirred for 2.5 h at rt. Column chromatography on silica gel (eluting with 10% EtOAc/hexanes) afforded the product as a pale yellow liquid (190 mg, 95%).

Sources & evidence

ORD record
ord-b103370ae3684791a76d208c5de241f6
Source dataset
uspto-grants-2014_07
Patent number
US08785665B2

Reaction notes

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