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Baran

Thursday, May 19th, 2011


Background music: Mozart
Syntheses discussed:

Et2N

H
N

OH
N

Cl

Cl

Cl

Valium (diazepam)

H
N

H
N

CO2K
N

Cl

Ph

Cl

Cl

Cl

H
N

CO2H
O

MeN

Me

Br

NH

MeHN

N
O
N
Me

N
H
OMe

Verstran (prazepam)

Et
N
NMe

N
N

Cl
Ph

N
O

H
N

Cl

Me
N

Cl
Ph
Ac

Ph

Ac2O, py

NH
Cl

Ac
N

H
N

MeOH, NaOH,
OAc
N

Cl

OMe

Cl
Ph

Ph

H
N
N

Cl

H3O+

H
N

OMe

NH2

Cl
Ph

NH

NH2

NHMe
N
H

Cl

NaOH
O

N
H

Ac2O, NaOAc

NH

CHCl2

Ph

Lotrafiban
GSK, OPRD 2003, 7, 655

Partial list of concepts/transforms discussed:


Sternbach
Beckmann mixture
Boekelheide reaction
Problems of the day:
N

O2N

pyridobenzodiazepines
JMC 2002, 45, 5136

Zyprexa (olanzapine)
Eli Lilly
see Lecture 5

N
H

Ph O

O2N

Ph

NH

AS-8112
Dainippon, OPRD 2002, 6, 28

Reading assignment: Handouts

H3O+

CONHMe

Ativan (lorazepam)

Clonopin (clonazepam)

Cl

Ph

Cl
O2N

Tranxene
(clorazepate)

NHAc

2) NH3

Ph

Cl

H
N

1) Ac2O

OH
N

O2N

Ph

Cl

H
N

NHOH
NH

Dalmane (flurazepam)

Serax (oxazepam)

HCl

Librium
(chlordiazepoxide)

H
N

Cl

Serax

HO

NaOH

Ph

Cl

Me

NHMe

Cl
NH

Some of Leo Sternbach's Drugs (Roche):

H
N

Heterocyclic
Chemistry

Lecture 19: Benzodiazepines