BOC-THIONOPHE-1-(6-NITRO)BENZOTRIAZOLIDE synthesis
- Product Name:BOC-THIONOPHE-1-(6-NITRO)BENZOTRIAZOLIDE
- CAS Number:184951-87-9
- Molecular formula:C20H21N5O4S
- Molecular Weight:427.48
To a solution of thioanilide 7 (2 mmol) dissolved by gentle warming at 40 °C and then cooled to 0 °C in glacial acetic acid (diluted with 5% water, 15 mL) was added NaNO2 (0.21 g, 3 mmol) in portions over 5 min with stirring. After 30 min, ice water (～100 mL) was added, and the precipitated product was filtered and washed with water. The orange solid was dried in vacuo at rt overnight and then at 50 °C for 4 h to afford benzotriazoles 1-(N-BOC-L-thionophenylalaninyl)-6-nitrobenzotriazole (9b): yield 81%. as amorphous solids of sufficient purity for use in the next step.
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Yield:-
Steps:
Multi-step reaction with 3 steps
1: 1.) N-methylmorpholine, isobutyl chloroformate / 1) THF, -20 deg C, 10 min; 2) THF, -15 deg C, 2 h, rt, overnight
2: 87 percent / P4S10, Na2CO3 / tetrahydrofuran / 1) 0 deg C, 30 min, 2.) rt, 2.5 h
3: 81 percent / NaNO2 / acetic acid; H2O / 0.5 h / 0 °C
References:
Ashraf Shalaby;Grote, Christopher W.;Rapoport, Henry [Journal of Organic Chemistry,1996,vol. 61,# 25,p. 9045 - 9048]
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184951-87-9
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