TERT-BUTYL N-[5-(TOSYLOXY)PENTYL]CARBAMATE synthesis
- Product Name:TERT-BUTYL N-[5-(TOSYLOXY)PENTYL]CARBAMATE
- CAS Number:118811-34-0
- Molecular formula:C17H27NO5S
- Molecular Weight:357.46
75178-90-4
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118811-34-0
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Yield:118811-34-0 91%
Reaction Conditions:
with dmap;triethylamine in dichloromethane at 0 - 20; for 4.5 h;
Steps:
5-((tert-butoxycarbonyl)amino)pentyl 4-methylbenzenesulfonate (13-3).
To a stirred solution of 13-2 (1.97 g, 9.7 mmol) in CH2Cl2 (32 mL) on ice was added TsCl (2.78 g, 14.6 mmol), Et3N (4.0 mL, 28.9 mmol) and DMAP (117.4 mg, 0.96 mmol). After being stirred for 4.5 h, the reaction mixture was diluted with CHCl3, washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was subjected to flash column chromatography (SiO2, n-hexane/EtOAc = 1:0, 8:1, and then 4:1) to obtain 13-3 (3.14 g, 91%). 1H NMR (500 MHz, CDCl3) δ 7.76 (d, J = 8.2 Hz, 2H), 7.33 (d, J = 8.2 Hz, 2H), 4.51 (broad s, 1H), 4.00 (t, J = 6.5 Hz, 2H), 3.06-3.02 (broad q, J = 6.5 Hz, 2H), 2.44 (s, 3H), 1.67-1.61 (m, 2H), 1.42-1.38 (m, 11H), 1.35-1.29 (m, 2H); HRMS (ESI, positive) m/z 380.1497 [M+Na]+ (calcd for C17H27NO5S 380.1502).
References:
Otsuki, Satsuki;Nishimura, Shinichi;Takabatake, Hisae;Nakajima, Kozue;Takasu, Yasuaki;Yagura, Toru;Sakai, Yuki;Hattori, Akira;Kakeya, Hideaki [Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,# 6,p. 1608 - 1611] Location in patent:supporting information
75178-90-4
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$8.00/250mg
104-15-4
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118811-34-0
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$87.50/250mg
24424-99-5
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118811-34-0
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$87.50/250mg
2508-29-4
202 suppliers
$11.00/5g
118811-34-0
39 suppliers
$87.50/250mg
2508-29-4
202 suppliers
$11.00/5g
24424-99-5
816 suppliers
$13.50/25G
75178-90-4
123 suppliers
$8.00/250mg
98-59-9
586 suppliers
$9.00/5g
118811-34-0
39 suppliers
$87.50/250mg