tert-Butyl 2-iodoacetate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add a solution of 7.35 g. 3-bromoperhydroazonin-2-one [Nagasawa et al., J. Med. Chem., 14, 501 (1971)]and 8.47 g t-butyl iodoacetate in 70 ml THF to a suspension of 0.881 g sodium hydride in 35 ml THF. After 2 hours at room temperature, add 15 ml saturated NH4Cl solution, filter and concentrate the filtrate in vacuo. Partition the residue between ether and H2O and wash the organic phase with H2O and brine. Dry the ether solution and filter. Decolorize the filtrate with charcoal, filter and concentrate the filtrate in vacuo to isolate 3-bromo-1-t-butoxycarbonylmethylperhydroazonin-2-one. Purify a sample for characterization by silica gel chromatography. Anal. C14H24BrNO3). Calc: C, 50.31; H, 7.24; N, 4.18; Br, 23.91. Found: C, 49.86; H, 7.33; N, 4.30; Br, 23.51. Mass spectrum: M+ at 334; m/e: 278 (M+ --C 4 H8); 261 (M+ --C4H9O); 232 (M+ --C4H9CO2 --H, base). Add a solution of 7.35 g filter concentrate the filtrate in vacuo Partition the residue between ether and H2O wash the organic phase with H2O and brine Dry the ether solution filter filter concentrate the filtrate in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add a solution of 7.35 g. 3-bromoperhydroazonin-2-one [Nagasawa et al., J. Med. Chem., 14, 501 (1971)]and 8.47 g t-butyl iodoacetate in 70 ml THF to a suspension of 0.881 g sodium hydride in 35 ml THF. After 2 hours at room temperature, add 15 ml saturated NH4Cl solution, filter and concentrate the filtrate in vacuo. Partition the residue between ether and H2O and wash the organic phase with H2O and brine. Dry the ether solution and filter. Decolorize the filtrate with charcoal, filter and concentrate the filtrate in vacuo to isolate 3-bromo-1-t-butoxycarbonylmethylperhydroazonin-2-one. Purify a sample for characterization by silica gel chromatography. Anal. C14H24BrNO3). Calc: C, 50.31; H, 7.24; N, 4.18; Br, 23.91. Found: C, 49.86; H, 7.33; N, 4.30; Br, 23.51. Mass spectrum: M+ at 334; m/e: 278 (M+ --C 4 H8); 261 (M+ --C4H9O); 232 (M+ --C4H9CO2 --H, base). Add a solution of 7.35 g filter concentrate the filtrate in vacuo Partition the residue between ether and H2O wash the organic phase with H2O and brine Dry the ether solution filter filter concentrate the filtrate in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: React 5.65 g of this azide with 7.9 g t-butyl iodoacetate and 0.82 g sodium hydride as described in Example 1 to obtain 1-t-butoxycarbonylmethyl-3-azido-8-methylperhydroazocin-2-one, which can be purified by chromatography over silica gel. NMR (CCl4, TMS): δ 1.0-2.2 (m); δ 1.3 (d); δ 1.45 (s); δ 3.45 (d, J=16h3); δ 3.95 (d, J-16h3); δ 4.3-5.1 (m).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: React 5.65 g of this azide with 7.9 g t-butyl iodoacetate and 0.82 g sodium hydride as described in Example 1 to obtain 1-t-butoxycarbonylmethyl-3-azido-8-methylperhydroazocin-2-one, which can be purified by chromatography over silica gel. NMR (CCl4, TMS): δ 1.0-2.2 (m); δ 1.3 (d); δ 1.45 (s); δ 3.45 (d, J=16h3); δ 3.95 (d, J-16h3); δ 4.3-5.1 (m).

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of phenyl acridine-9-carboxylate (100 mg) and t-butyl iodoacetate is stirred and heated at 110° C. for five hours. The resulting solution is poured into diethyl ether (25 ml) and the resulting precipitate isolated by filtration. Part of this precipitate (10 mg) is stirred with 33% hydrobromic acid in acetic acid (1 ml), and heated at 50° C. for two hours. The reaction mixture is poured into water, and the resulting precipitate (ca. 6 mg) isolated. MS: 358, 314, 300, 237, 220, 206. the resulting precipitate isolated by filtration heated at 50° C. for two hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of t-butyl chloroacetate (20 g) and sodium iodide (25 g) is stirred in acetone (200 ml) for twenty hours. The acetone is removed by distillation under reduced pressure. The residue is partitioned between diethyl ether (100 ml) and water (50 ml). The ether layer is washed with water, 5% sodium thiosulfate solution, and water. The organic layer is dried over sodium sulfate, and evaporated under reduced pressure. There is obtained 25 grams of t-butyl iodoacetate. NMR: 63.5, 1.38. The acetone is removed by distillation under reduced pressure The residue is partitioned between diethyl ether (100 ml) and water (50 ml) The ether layer is washed with water, 5% sodium thiosulfate solution, and water The organic layer is dried over sodium sulfate evaporated under reduced pressure