3-(4-Hydroxyphenyl)propionic acid → 2-[3-(4-Hydroxyphenyl)propionylamino]pentanedioic acid diethyl ester

HRID 1354382Notes

Reaction equation

HRID 1354382 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[CH2:13]([O:15][C:16](=[O:26])[C@H:17]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[NH2:18])[CH3:14]>>[CH2:13]([O:15][C:16](=[O:26])[CH:17]([NH:18][C:10](=[O:12])[CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH3:14]

Participants

3

Reactant 2

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 73961Glutamic acid diethyl ester

Product 1

HCID 694190032-[3-(4-Hydroxyphenyl)propionylamino]pentanedioic acid diethyl esterYield 90.1%

Procedure

Following the same procedure of Example 4 except that 3-(4-hydroxyphenyl)propionic acid (1.0 g, 6.0 mmol) and glutamic acid diethyl ester (1.34 g, 6.6 mmol) were used, 1.9 g of the title compound was obtained. The compound was finally purified by silica gel column chromatography (column size: 25 mm×150 mm, silica gel 70-230 mesh, eluent: hexane/EtOAc (1/1)). The results of analyses of the compound are as follows:

Sources & evidence

ORD record
ord-af5f4bd116b5453cb69af602af3cd8d8
Source dataset
uspto-grants-2007_05
Patent number
US07223793B2

Reaction notes

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