ChemicalBook CAS DataBase List Carbamic acid, (2,2-dimethyl-3-oxopropyl)-, 1,1-dimethylethyl ester (9CI)

Carbamic acid, (2,2-dimethyl-3-oxopropyl)-, 1,1-dimethylethyl ester (9CI) synthesis

4synthesis methods

Product Name:Carbamic acid, (2,2-dimethyl-3-oxopropyl)-, 1,1-dimethylethyl ester (9CI)
CAS Number:195387-13-4
Molecular formula:C10H19NO3
Molecular Weight:201.26

102520-97-8
116 suppliers
$7.00/1g

Carbamic acid, (2,2-dimethyl-3-oxopropyl)-, 1,1-dimethylethyl ester (9CI)

195387-13-4
18 suppliers
$310.00/100mg

Yield:195387-13-4 95.1%

Reaction Conditions:

with sodium hypochlorite;2,2,6,6-Tetramethyl-1-piperidinyloxy free radical;potassium bromide in dichloromethane;water at -10 - 0; for 0.583333 h;NaHCO₃ buffer;

Steps:

51

Procedure 18: Synthesis of Aldehydes via TEMPO/Bleach OxidationTo a vigorously stirring solution of the alcohol (1.54 mmol) in DCM (4 mL) was added TEMPO (0.007 g, 0.045 mmol, 0.03 mol %) and a 2M aqueous KBr solution (75 mL, 0.15 mmol, 10 mol %) and the reaction mixture was cooled to -10°C.In a separate flask NaHCO₃ (0.5 g, 9.5 mmol) was dissolved in bleach (25 mL, Chlorox 6.0% NaOCl) to yield a 0.78 M buffered NaOCl solution. This freshly prepared 0.78 MNaOCl solution (2.3 mL, 1.8 mmol, 117 mol %) was added to the reaction mixture over 5 min and the reaction was stirred for an additional 30 min at 0°C. The organic phase was separated and the aqueous layer was extracted with dichloromethane (2 x 4 mL). The combined organic layers were washed with 10% aq. Na₂S₂O₃ (4 mL), sat. aq. NaHCO₃ (2 x 4 mL), brine (5 mL), dried over Na₂SO₄ and concentrated to dryness. Example 51 6'-(2,2-Dimethyl-3-amino-propyl)-l-(3-amino-2(5)-hydroxy-propionyl)-sisomicinN-Boc-2,2-dimethyl-3-amino-propionaldehyde N-Boc-2,2-dimethyl propanol (0.415 g, 2.04 mmol) was submitted toProcedure 18 to yield N-Boc-2,2-dimethyl-3-amino-propionaldehyde (0.39 g, 1.94 mmol, 95.1 % yield): ¹H NMR (250 MHz, CDC13) δ 9.42 (s, 1 H), 4.80 (bs, 1 H), 3.11 (d, 2 H), 1.39 (s, 9 H), 1.06 (s, 6 H).

References:

WO2009/67692,2009,A1 Location in patent:Page/Page column 45-46; 179

Carbamic acid, (3-hydroxy-2,2-dimethylpropyl)-, 1,1-dimethylethyl ester (9CI)

184357-44-6
46 suppliers
$60.00/100mg

195387-13-4
18 suppliers
$310.00/100mg

References

26734-09-8
114 suppliers
$35.28/1g

195387-13-4
18 suppliers
$310.00/100mg

References

24424-99-5 Synthesis

24424-99-5
831 suppliers
$13.50/25G

195387-13-4
18 suppliers
$310.00/100mg

References