ChemicalBook CAS DataBase List Glycine, N-3-buten-1-yl-N-(phenylmethyl)-, methyl ester

Glycine, N-3-buten-1-yl-N-(phenylmethyl)-, methyl ester synthesis

3synthesis methods

Product Name:Glycine, N-3-buten-1-yl-N-(phenylmethyl)-, methyl ester
CAS Number:175227-10-8
Molecular formula:C14H19NO2
Molecular Weight:233.31

17150-62-8
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Glycine, N-3-buten-1-yl-N-(phenylmethyl)-, methyl ester

175227-10-8
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Yield:175227-10-8 84%

Reaction Conditions:

with triethylamine in dimethyl sulfoxide; for 1 h;

Steps:

1B Example-1B

To a 10 ml round bottom flask was added the product of Example 1A (3.57 g, 22.1 mmol), dimethyl sulfoxide (30 ml) and triethylamine (3.70 ml, 26.6 mmol). Methyl bromoacetate (2.3 ml, 24 mmol) was added dropwise and the reaction mixture was allowed to stir for 1h. The mixture was poured into ethyl acetate (50 ml) washed with water (50 ml) and brine (50 ml) dried over anhydrous Na2SO4 filtered and concentrated in vacuo. The crude material was purified via column chromatography (SiO2, heptane/ethyl acetate 0-10% gradient over 60 minutes) to give the title compound (4.33 g, 18.6 mmol, 84% yield). H1 NMR (500 MHz, DMSO-d6) δ ppm 7.51-7.10(m, 5H), 5.81(ddt, J=17.0,10.2,6.8 Hz, 1H), 5.08-4.92(m, 2H), 4.03(q, J=7.1 Hz, 1H), 3.81(s, 1H), 3.24(dd, J=195.9,87.8 Hz, 1H), 2.85(d, J=10.3 Hz, 1H), 2.80-2.59(m, 1H), 2.45-2.25(m, 2H), 2.18(q, J=7.0 Hz, 2H), 2.13-1.74(m, 2H); MS (DCI) m/z 234 [M+H]+

References:

US2016/264582,2016,A1 Location in patent:Paragraph 0286

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