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O
O
O
O
O
O
HCOOH
DCC
N
N
S
S
HN
CHO
H 2 N
H
H
221
222
O
O
N
1. CH 2 Cl 2 , O
O
N
2. COCl 2 , -50°C
S
CN
H
223
ONa
O
O
S
O
N
S
N
H
224
O
H
Temocillin disodium
O
a
Zileuton [111406-87-2], anti-inflammatory, antiasthmatic, 5-lipoxygenase inhibitor, 229.
Phosgene or phosgene equivalents (trimethylsilyl isocyanate, diisopropyl azodi-
carboxylate) have been employed to prepare the hydroxy-urea compound Zileuton
[163-169].
HO
HO
COCl 2 , toluene
HCl, NH 3
or Me 3 SiNCO,
dioxane, NH 3
N
CO
NH 2
S
NH
S
NH 3
tBuOH
229
225
Zileuton
Ph 3 P, THF,
diisopropyl
azodicarboxylate
O
OH
S
O
OC
O
O
O
HN
O
S
N
O
O
O
226
227
228
 
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