Triethylamine → 3-(2-Ethoxycarbonyl-acetylamino)-2-phenyl-propionic acid ethyl ester

HRID 1180088Notes

Reaction equation

Cl.[NH2:2][CH2:3][CH:4]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(N(CC)CC)C.Cl[C:24](=[O:31])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>C(Cl)Cl>[CH2:8]([O:7][C:5](=[O:6])[CH:4]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:3][NH:2][C:24](=[O:31])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl 3-amino-2-phenylpropanoate hydrochloride (4.38 g, 19.13 mmol) was suspended in methylene chloride (80 mL) and triethylamine (5.86 mL, 2.2 eq.). The mixture was cooled to 0° C. and treated dropwise with ethyl 3-chloro-3-oxopropanoate (2.69 mL, 1.1 eq.). The reaction was kept at room temperature for one hour, diluted with methylene chloride, washed with 1 N HCl and then with 5% NaHCO3, dried over Na2SO4 and evaporated to dryness. The crude material was chromatographed on silica gel, eluting with hexane/ethyl acetate 1/1, to give 3-(2-ethoxycarbonyl-acetylamino)-2-phenyl-propionic acid ethyl ester (4.24 g, Y=72%) as an oil.

Workup

washwashed with 1 N HCl
dry with materialwith 5% NaHCO3, dried over Na2SO4
customevaporated to dryness
customThe crude material was chromatographed on silica gel
washeluting with hexane/ethyl acetate 1/1

Sources & evidence

ORD record: ord-2da5e49203d3412c92191bbce721cb45
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279575B2

Reaction notes

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