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General Experimental
Procedure for the Preparation of Azidoformates: To a stirred
solution of alcohol (1 mmol) and sodium azide (2 mmol) in acetone
(10 mL) was added triethylamine (1.5 mmol) at 0 °C. The
reaction mixture was stirred at this temperature for 15 min and
a solution of triphosgene (0.5 mmol) in acetone (5 mL) was added dropwise
at 0 °C over about 15 min. The reaction mixture was stirred
at this temperature for 1 h and slowly allowed to warm up to room
temperature. It was stirred for 24 h at room temperature. The reaction
mixture was filtered to remove insoluble salts and the filtrate
was diluted with an equal volume of water. It was extracted with
EtOAc (3 × 20 mL) and the organic extract was washed with
water (10 mL) and brine (10 mL) and dried (Na2SO4).
The solvent was removed and the residue was purified by column chromatography
to get pure azidoformate in good yield (Table
[1]
). [CAUTION: We did not observe any untoward
incidence while working with azidoformates. However, the use of
hood and safety shield is recommended as tert-butyl
azidoformate is known to decompose above 80 °C with apparent
detonation.
[13]
].
Spectral
data for benzyl azidoformate 1H NMR (CDCl3, 200MHz): δ 5.25
(s, 2 H), 7.45 (s, 5 H); IR (KBr, CHCl3) 2166, 2140,
1736, 1498, 1456, 1377, 1236 cm-1;
Anal. Calcd for C8H7N3O2:
C, 54.23; H, 3.98; N, 23.71. Found: C, 54.47; H, 3.95; N, 23.67.
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General Experimental
Procedure for the Synthesis of N-Carbobenzyloxy-β-lactams (4a-f): To a solution of benzyl azidoformate
(1 mmol) in toluene (10 mL) was added triphenyl phosphine (1 mmol)
and the reaction mixture was stirred at room temperature for 3 h.
Aldehyde (1 mmol) was added to the reaction and refluxed for 8-10
h. Solvent was removed under reduced pressure and dry diethyl ether
(15
mL) was added to the residue. The solid triphenyl phosphineoxide
separated was removed by filtration and the solvent was removed
to get imine 3. These imines were found
to be unstable and used further without purification.
A
solution of above imine (1 mmol) in dichloromethane (15 mL) and
triethylamine (4 mmol) was cooled to 0 °C and a solution
of acid chloride in CH2Cl2 (10 mL), was added slowly
with stirring in about 20 min. The reaction mixture was allowed
to warm up to room temperature and stirred for 18 h. It was washed
with water (15 mL), saturated sodium bicarbonate solution (10 mL),
brine (10 mL) and dried over sodium sulfate. Solvent was removed
under reduced pressure and the crude product was purified by column chromatography
to get β-lactams 4a-f in good yield.
Spectral data
for β-lactam (4a): 1H
NMR (CDCl3, 200 MHz): δ 3.87 (d, J = 14.7 Hz, 1 H), 4.75 (d, J = 4.4 Hz, 1 H), 4.91 (d, J = 14.7 Hz, 1 H), 5.40 (d, J = 4.4 Hz, 1 H), 6.70 (d, J = 7.8 Hz, 2 H), 6.85 (t, J = 7.8 Hz, 1 H), 7.10-7.33
(m, 12 H); 13C NMR (CDCl3,
50.3 MHz) 44.10, 61.34, 82.04, 115.45, 121.84, 127.84, 128.13, 128.53,
128.76, 129.05, 132.61, 134.67, 156.80, 159.56, 165.48; IR (KBr,
CHCl3) 1758, 1596, 1494, 1236 cm-1;
Anal. Calcd for C23H19NO4: C, 73.98;
H, 5.12; N, 3.75. Found: C, 73.79; H, 4.98; N, 3.77.
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