ChemicalBook CAS DataBase List TERT-BUTYL 3-(ETHOXYCARBONYL)-2-OXOPROPYLCARBAMATE

TERT-BUTYL 3-(ETHOXYCARBONYL)-2-OXOPROPYLCARBAMATE synthesis

7synthesis methods

Product Name:TERT-BUTYL 3-(ETHOXYCARBONYL)-2-OXOPROPYLCARBAMATE
CAS Number:67706-68-7
Molecular formula:C11H19NO5
Molecular Weight:245.27

4530-20-5

6148-64-7

TERT-BUTYL 3-(ETHOXYCARBONYL)-2-OXOPROPYLCARBAMATE

67706-68-7

(1) Carbonyldiimidazole (10.2 g, 63.1 mmol) was added to a suspension of 2-(tert-butoxycarbonylamino)acetic acid (10 g, 57.1 mmol) in tetrahydrofuran (100 mL) and the reaction was stirred at room temperature for 2 hours. Subsequently, magnesium chloride (5.4 g, 57.1 mmol) and monoethyl malonate potassium salt (9.7 g, 57.1 mmol) were sequentially added to the reaction system and stirring was continued for 1 h at 60 °C. The reaction was completed by filtration. After completion of the reaction, the insoluble material was removed by filtration, and the filtrate was diluted with ethyl acetate (200 mL), washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride in turn, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography [eluent: n-hexane-ethyl acetate (2:1)] to afford ethyl 4-(tert-butoxycarbonylamino)-3-oxobutanoate (11.9 g, 48.5 mmol, 85% yield) as a colorless oil.1H-NMR (CDCl3) δ: 1.29 (3H, t, J = 7.4 Hz), 1.45 (2H, s) , 3.87 (2H, s), 3.96 (3H, s), 4.21 (2H, q, J = 7.2 Hz), 7.08 (1H, d, J = 8.7 Hz), 7.39 (9H, s), 3.49 (2H, s), 4.14 (2H, d, J = 5.8 Hz), 4.21 (2H, q, J = 7.4 Hz), 5.15-5.24 (1H, br).

4530-20-5 Synthesis

4530-20-5
572 suppliers
$5.00/5 g

67706-68-7
36 suppliers
$62.00/250mg

Yield:-

Steps:

Multi-step reaction with 2 steps
1: triethylamine / tetrahydrofuran / 0.5 h / -30 - -20 °C
2: 1.) diisopropylamine, n-BuLi / 1.) THF, -70 deg C, 30 min, 2.) THF, -65 deg C, 20 min

References:

Kim, Hwa-Ok;Olsen, Richard K.;Choi, Ok-Soon [Journal of Organic Chemistry,1987,vol. 52,# 20,p. 4531 - 4536]

4530-20-5 Synthesis

4530-20-5
572 suppliers
$5.00/5 g

6148-64-7 Synthesis

6148-64-7
411 suppliers
$5.00/10g

67706-68-7
36 suppliers
$62.00/250mg

References

24424-99-5 Synthesis