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. Author manuscript; available in PMC: 2018 Jan 26.
Published in final edited form as: Chem Res Toxicol. 2016 Dec 6;29(12):2194–2205. doi: 10.1021/acs.chemrestox.6b00384

Scheme 2.

Scheme 2

Synthesis of Nitrosamides (A) Methyl Acrylate, NaCN, DMF, 40 °C, 4h; (B) NaOH, H2O, RT, 3h; (C) EDAC, NHS, MeNH2•HCl, DMSO, RT, 22h; (D) NaNO2, Ac2O:HOAc, 0 °C, 4h; (E) HS(CH2)3SH, BF3•OEt2, THF, 80 °C, 24h; (F) (i) n-BuLi, TMEDA, THF, −78 °C, 1h; (ii) 27, THF, −78 °C to RT, 16h; (G) 25% TFA, CH2Cl2, RT, 3h; (H) HCO2Me, Et3N, MeOH, 55 °C, 4h; (I) AgNO3, NCS, MeCN:H2O (1:1), 0 °C, 30 min; (J) Boc2O, Et3N, CH2Cl2, RT, 30 min; (K) I2, PPh3, Im., CH2Cl2, 0 °C-RT, 22h.