ChemicalBook CAS DataBase List TERT-BUTYL N-[5-(TOSYLOXY)PENTYL]CARBAMATE

TERT-BUTYL N-[5-(TOSYLOXY)PENTYL]CARBAMATE synthesis

6synthesis methods

Product Name:TERT-BUTYL N-[5-(TOSYLOXY)PENTYL]CARBAMATE
CAS Number:118811-34-0
Molecular formula:C17H27NO5S
Molecular Weight:357.46

75178-90-4 Synthesis

75178-90-4
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$8.00/250mg

98-59-9 Synthesis

98-59-9
586 suppliers
$9.00/5g

TERT-BUTYL N-[5-(TOSYLOXY)PENTYL]CARBAMATE

118811-34-0
36 suppliers
$87.50/250mg

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 Synthesis

75178-90-4
122 suppliers
$8.00/250mg