sodium hydrogencarbonate in N-methyl-acetamide

1: 89 percent / Et3N / ethyl acetate / 4 h / Heating 2: 100 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene (DBU) / tetrahydrofuran / 0.5 h / 0 °C 3: 1.) N-hydroxysuccinimide, N,N-dicyclohexylcarbodiimide (DCC) / 1.) THF, 15 min, 2.) RT, 3 days 4: 95 percent / sat NaHCO3 aq / 0.67 h / Heating 5: 25 percent / PCl5, CaCO3 / nitromethane / 0.67 h / Heating 6: 61 percent / aluminium amalgam / diethyl ether; H2O / 1 h / Heating 7: 1.) oxalyl chloride, 2.) 4N HCl / 1.) DMF, benzene, reflux, 3.5 min,then RT, 2.) acetone, RT, 5h 8: lithium hydroxyde monohydrate / H2O 9: 57 percent / lithium hydroxide monohydrate / H2O; acetone / 2 h 10: 84 percent / potassium dihydrogen phosphate, 1N LiOH, hog kidney acylase I / H2O / 24 h View Scheme

1: 91 percent / Et3N / ethyl acetate / 2 h / Heating 2: 99 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene (DBU) / tetrahydrofuran / 0.5 h / 0 °C 3: 1.) N-hydroxysuccinimide, N,N-dicyclohexylcarbodiimide (DCC) / 1.) THF, 2.) RT 4: 57 percent / thiophenol, Zn-Cu complex / dimethylformamide / 1 h / 65 °C 5: 86 percent / 1N NaOH / H2O / 0.67 h / Heating 6: 43 percent / anhyd liquid ammonia, Li / Heating View Scheme

Multi-step reaction with 2 steps 1: 90 percent2: DBU / tetrahydrofuran / 0 °C  

Multi-step reaction with 2 steps 1: 84 percent / Et3N / dimethylformamide / 2 h / 90 °C2: 98 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene (DBU) / tetrahydrofuran / 0.5 h / 0 °C  

Multi-step reaction with 4 steps 1: 90 percent2: DBU / tetrahydrofuran / 0 °C3: 60 percent4: 45 percent / Zn(Cu), benzenethiol / dimethylformamide  

Multi-step reaction with 2 steps 1: 89 percent / Et3N / ethyl acetate / 4 h / Heating2: 100 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene (DBU) / tetrahydrofuran / 0.5 h / 0 °C