Synthesis of Hyrtiazepine

Structure of Hyrtiazepine

C20H15N3O4

Principal investigatorKentaro Yamaguchi
Publication year2011
Synthesis typeTotal
Number of steps 14 (3 parts)
References
Part 1 of 3
intermediate structure
NaH, TsCl
THF
RT, 3 h, 94%
intermediate structure
Part 2 of 3
intermediate structure
Imidazole, TBSCl
DMF
RT, 30 min
intermediate structure
NaH, TsCl
THF
RT, 2 h
intermediate structure
HCl
H2O, THF
Reflux, 2 h, 78 % (3 steps)
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
PhB(OH)2, EtCO2H
Dean-Stark
PhMe
Reflux, 24 h, 77%
intermediate structure
MeI, K2CO3
DMF
RT, 2 h, 75%
intermediate structure
IBX
DMSO
RT, 2 h, 86%
intermediate structure
KOH
MeOH, THF
Reflux, 2 h, 86%
intermediate structure
TsCl, Et3N
CH2Cl2
RT, 7 h, 85%
intermediate structure
Special reagent
Ac2O
AcOH
80 °C, 3 h, 68%
intermediate structure
EtI, K2CO3
DMF
RT, 2 h, 82%
intermediate structure
HCl
EtOH, H2O
Reflux, 20 h, 70%
intermediate structure
BBr3
CH2Cl2
Reflux, 2 h, 80%
intermediate structure
K2CO3
MeOH
Reflux, 3 h, 65%
intermediate structure