Chemistry Reference
In-Depth Information
The monochlorinated vinylene carbonate is also used in the synthesis of Cefcanel,a
new cephalosporin from Kyoto and Astra [112, 113].
Lisinopril [76547-98-3], angiotensin-converting enzyme inhibitor ( for use as antihyperten-
sive and in congestive heart failure), 149.
Phosgenation is employed to activate N
6
-
(trifluoroacetyl)-l-lysine 146 as N
2
-carboxy anhydride 147, a key intermediate in the
acylation of
l-proline [114, 115]. Alternative processes have also been described
[116-119].
O
O
COCl
2
,
THF, 10-20°
C
N
H
CF
3
N
H
CF
3
HN
H
2
N
H
O
O
O
146
147
O
HO
O
O
O
NH
2
N
H
CF
3
O
O
N
H
N
H
N
N
COOH
COOH
149
Lisinopril
148
Meprobamate [57-53-4], tranquilizer, 152. 2-Methyl-2-propyl-1,3-propanediol dicar-
bamate (Meprobamate) 152 is prepared by phosgenation of the corresponding diol
151 [120].
O
NH
2
1.
COCl
2
2. NH
3
OH
O
O
HCHO
OH
O
NH
2
CHO
150
151
152
Meprobamate
Mezlocillin [51481-65-3], antibiotic, 156.
Chloroformylation of 1-methanesulfonyl-
2-imidazolidinone 153 with phosgene results in the key intermediate, 3-chloro-
formyl-1-methanesulfonyl-2-imidazolidinone 154 [121-125].
Nefazodone hydrochloride [82752-99-6], antidepressant, 5-HT
2
A-antagonist, 163.
In
one method, phosgenation is applied to prepare the key intermediate 2,4-dihydro-
3H-1,2,4-triazol-3-one 161 [126].
