3-(4-Hydroxyphenyl)propionic acid → 2-[3-(4-Hydroxyphenyl)propionylamino]-3-methyl butyric acid methyl ester

HRID 1354385Notes

Reaction equation

HRID 1354385 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.Cl.[CH3:14][O:15][C:16](=[O:22])[C@H:17]([CH:19]([CH3:21])[CH3:20])[NH2:18]>>[CH3:14][O:15][C:16](=[O:22])[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)[CH:19]([CH3:21])[CH3:20]

Participants

3

Reactant 2

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 111190Methyl valinate hydrochloride

Product 1

HCID 117783682-[3-(4-Hydroxyphenyl)propionylamino]-3-methyl butyric acid methyl esterYield 89.5%

Procedure

Following the same procedure of Example 4 except that 3-(4-hydroxyphenyl)propionic acid (1.0 g, 6.0 mmol) and valine methyl ester hydrochloride (1.1 g, 6.6 mmol) were used, 1.5 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-619f693a82844c9da71294fc05e60b99
Source dataset
uspto-grants-2007_05
Patent number
US07223793B2

Reaction notes

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