Tert-Butyl N-(3-[(Tert-Butyldimethylsilyl)Oxy]-2-Oxopropyl)Carbamate synthesis

4synthesis methods

Product Name:Tert-Butyl N-(3-[(Tert-Butyldimethylsilyl)Oxy]-2-Oxopropyl)Carbamate
CAS Number:184429-84-3
Molecular formula:C14H29NO4Si
Molecular Weight:303.47

tert-butyl 3-(tert-butyldimethylsilyloxy)-2-hydroxypropylcarbamate

195197-94-5
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Tert-Butyl N-(3-[(Tert-Butyldimethylsilyl)Oxy]-2-Oxopropyl)Carbamate

184429-84-3
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$45.00/250mg

Yield: 92%

Reaction Conditions:

Stage #1:[3-(tert-butyldimethylsilanyloxy)-2-hydroxypropyl]carbamic acid tert-butyl ester with oxalyl dichloride;dimethyl sulfoxide in dichloromethane for 1.33333 h;Inert atmosphere;Cooling with ice;
Stage #2: with triethylamine in dichloromethane at 20;Inert atmosphere;

Steps:

1 Preparation of terf-butyl 3-(tert-butyldimethylsilyloxy)-2-oxopropylcarbamate
To a stirring solution of oxalyl chloride (13.6 mL, 0.16 mol) in dry CH₂Cl₂ (150 mL) at -78°C under N₂ was added DMSO (15.2 mL, 0.21 mol) dropwise over 30 min. After complete addition the resulting solution was stirred at -78°C for 1 h. A solution of tert-butyl 3-(rt-butyldimethyl-silyloxy)-2-hydroxypropylcarbamate (32.6 g, 0.1 1 mol) in CH₂Cl₂ (50 mL) was then added dropwise over 20 min. Stirring was continued for a further 1 hour at which time triethylamine (59.6 mL, 0.43 mol) was added. The cooling bath was removed and the reaction mixture was allowed to warm to room temperature. The reaction mixture was partitioned between water (100 mL) and CH₂Cl₂ (70 mL) and the aqueous layer was extracted with further CH₂Cl₂ (2 x 70 mL); the combined organics were dried over Na₂SO₄ and concentrated under a stream of nitrogen gas. The crude residue was purified over silica gel eluting with 5% ethylacetate in n-hexane to give tert- butyl 3-(tert-butyldimethylsilyloxy)-2-oxopropylcarbamate (29.8 g, 92%) as a pale yellow oil. ¹H-NMR (300 MHz; CDCl₃) ppm: 0.11 (6 H, s), 0.94 (9 H, s), 1.47 (9 H, s), 3.92 (2 H, s), 4.26 (2 H, d, J4.6 Hz), 5.22 (1 H, br s).

References:

PHARMAXIS LTD.;DEODHAR, Mandar;FINDLAY, Alison, Dorothy;FOOT, Jonathan, Stuart;JAROLIMEK, Wolfgang;MCDONALD, Ian, Alexander;ROBERTSON, Alan;TURNER, Craig, Ivan WO2013/163675, 2013, A1 Location in patent:Paragraph 00182

24424-99-5 Synthesis

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184429-84-3
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137618-48-5
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184429-84-3
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18162-48-6 Synthesis

18162-48-6
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184429-84-3
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