Glycine, N-formyl-N-methyl-, ethyl ester synthesis
- Product Name:Glycine, N-formyl-N-methyl-, ethyl ester
- CAS Number:89531-66-8
- Molecular formula:C6H11NO3
- Molecular Weight:145.16
52605-49-9
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109-94-4
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Yield:89531-66-8 85%
Reaction Conditions:
with potassium carbonate in ethanol at 20;
Steps:
1.2 4.1.1.2. Ethyl N-formyl-N-methylglycinate (3).
Ethyl N-methylglycinate hydrochloride salt (2) (30.0?g, 195?mmol) was suspended in a mixture of EtOH (200?mL) and ethyl formate (126?mL). Potassium carbonate (40.6?g, 294?mmol) was added under vigorous stirring and the suspension was stirred at rt overnight. The reaction mixture was then filtered and the precipitate was washed with EtOH (150?mL). The filtrate was concentrated and dissolved in a minimum amount of water (10?mL), followed by extraction with EtOAc (4?*?200?mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to afford compound 3 (24.3?g, 167?mmol) as a pale yellow liquid. Yield 85%; 1H NMR (CDCl3, 500?MHz) δ (two rotamers) 7.93 and 7.86 (s, 1H, CHO), 4.04 and 4.02 (q, 2H, 3J?=?7.2?Hz, CH2CH3), 3.91 and 3.85 (s, 2H, NCH2), 2.87 and 2.74 (s, 3H, NCH3), 1.12 and 1.10 (t, 3H, 3J?=?7.1?Hz, CH2CH3); 13C NMR (CDCl3, 75?MHz) δ (two rotamers) 168.76, 168.31 (CO2), 163.09, 162.85 (CHO), 61.62, 61.29 (OCH2CH3), 50.93, 45.72 (NCH2), 35.10, 30.76 (NCH3), 14.09 (OCH2CH3).
References:
Ghedira, Donia;Voissière, Aurélien;Peyrode, Caroline;Kraiem, Jamil;Gerard, Yvain;Maubert, Elise;Vivier, Magali;Miot-Noirault, Elisabeth;Chezal, Jean-Michel;Farhat, Farhat;Weber, Valérie [European Journal of Medicinal Chemistry,2018,vol. 158,p. 51 - 67]
141-53-7
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52605-49-9
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107-97-1
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64-17-5
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141-53-7
752 suppliers
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