2-azidoacetamide

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-azido-acetamide (1.40 g, 14 mmol), 30% aqueous (methanol free) formaldehyde (1.40 g, 14 mmol) and 1.0 N aqueous KOH (0.28 ml, 0.28 mmol) was stirred at 0° C for 4 hrs. To the reaction mixture 1.0 N aqueous HCl was added (pH=7) and the resulting mixture evaporated in vacuo. The residue was suspended in ethyl acetate (50 ml), the solution dried over magnesium sulfate, filtered and the filtrate concentrated to a volume of 5 ml. Chromatography on silica gel (63-200 μm, 18 g) with ethyl acetate afforded 2-azido-N-(hydroxymethyl)-acetamide as a colourless oil in 90% yield. NMR-spectrum in CDCl3: 3.6 (broad signal, 1H), 4.0 (s, 2H), 4.8 (d, 2H, J=6 Hz), 7.3 (broad signal 1H) ppm. the resulting mixture evaporated in vacuo the solution dried over magnesium sulfate filtered the filtrate concentrated to a volume of 5 ml

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

Procedure: The reaction was carried out similarly as described in the preparation of compound 101, using compound 432 (1.04 mmol) and compound 411 (1.5 mmol). The crude product was purified by continuous gradient flash chromatography using EtOAc/DCM/petroleum ether (40-60) 0:80:20, 0:100:0 and 10:90:0 as the eluent to afford the title compound as yellow solid. The crude product was purified by continuous gradient flash chromatography

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

Procedure: The reaction was carried out similarly as described in the preparation of compound 411, using compound 3-chloro-propane-1-sulfonic acid amide (19.0 mmol). The crude product was purified by continuous gradient flash chromatography using EtOAc/petroleum ether (40-60) 35:65 to 65:35 as the eluent to afford the title compound as colourless oil. The crude product was purified by continuous gradient flash chromatography

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

Procedure: The reaction was carried out similarly as described in the preparation of compound 101, using compound 407 (0.44 mmol) and compound 411. The crude product was purified by continuous gradient flash chromatography using MeOH/DCM 0:100 to 10:90 as the eluent to afford the title compound as yellow solid. 13C NMR (DMSO-d6) δ 194.9, 167.1, 158.7 (dd), 155.7 (dd), 149.3, 145.2, 139.8, 135.9, 133.7, 133.7, 131.7, 128.2, 127.1, 126.6, 126.4 (dd), 125.0, 124.2 (dd), 123.0, 114.9, 112.0 (dd), 111.8, 105.0 (dd), 51.5, 19.4 The crude product was purified by continuous gradient flash chromatography

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-azido-acetamide (1.40 g, 14 mmol), 30% aqueous (methanol free) formaldehyde (1.40 g, 14 mmol) and 1.0 N aqueous KOH (0.28 ml, 0.28 mmol) was stirred at 0° C for 4 hrs. To the reaction mixture 1.0 N aqueous HCl was added (pH=7) and the resulting mixture evaporated in vacuo. The residue was suspended in ethyl acetate (50 ml), the solution dried over magnesium sulfate, filtered and the filtrate concentrated to a volume of 5 ml. Chromatography on silica gel (63-200 μm, 18 g) with ethyl acetate afforded 2-azido-N-(hydroxymethyl)-acetamide as a colourless oil in 90% yield. NMR-spectrum in CDCl3: 3.6 (broad signal, 1H), 4.0 (s, 2H), 4.8 (d, 2H, J=6 Hz), 7.3 (broad signal 1H) ppm. the resulting mixture evaporated in vacuo the solution dried over magnesium sulfate filtered the filtrate concentrated to a volume of 5 ml