Synthesis of tert-Butyl azidoformate

Preparation of tert-Butyl azidoformate

Preparation of tert-Butyl azidoformate

Preparation of tert-Butyl azidoformate

The tert-Butyl carbazate (13.2 g, 100 mmol) is dissolved in a mixture of acetic acid (40 ml) and water (80 ml), the solution is stirred and cooled in an ice water bath and treated with sodium nitrite (7.6 g, 110 mmol)· added in small portions in the course of a few minutes. The reaction mixture is diluted with water (80 ml) and the oily product extracted into ether (twice, 80 ml each time). The extracts are washed with water (80 ml), 1 M sodium hydrogen carbonate(80 ml) and dried with magnesium sulfate. The ether is removed in the vacuum of a water aspirator at 140-150 mm on a water bath of 40-45 °C. The remaining dark oil, crude tert.butyl azidoformate (about 13 g) can be distilled at about 70 mm and a bath temperature of 90°C. The fraction which boils at 73-74 °C at 70 mm weighs 11.5 g (80 %).

The Practice of Peptide Synthesis, by M. Bodanszky, A. Bodanszky, 242, Springer Berlin Heidelberg (1984)

IUPAC Name

tert-butyl N-diazocarbamate

InChI

InChI=1S/C5H9N3O2/c1-5(2,3)10-4(9)7-8-6/h1-3H3

InChI Key

ISHLCKAQWKBMAU-UHFFFAOYSA-N

Canonical SMILES

CC(C)(C)OC(=O)N=[N+]=[N-]

Depositor-Supplied Synonyms

tert-Butyl azidoformate, tert-Butoxycarbonyl azide, 1070-19-5, t-butoxycarbonylazide, tert-Butyloxycarbonyl azide, CARBONAZIDIC ACID, 1,1-DIMETHYLETHYL ESTER, BOC-azide, t-butylazidoformate, t-butyl azidoformate, t-butyl carbonazidate, tertbutoxycarbonylazide, t-butoxycarbonyl azide, t-butoxylcarbonyl azide, tert-butoxycarbonylazide, tert.butoxycarbonylazide, tertbutoxycarbonyl azide, Azido tert-butoxymethanone, tert.-butoxycarbonyl azide, azido(tert-butoxy)methanone, tert-butyl N-diazocarbamate, AC1L1UV0, 1,1-dimethylethoxy carbonylazide, CTK4A4909, ISHLCKAQWKBMAU-UHFFFAOYSA-N, tert-butyl (NE)-N-diazocarbamate, NSC95410, EINECS 213-972-8, NSC 95410, NSC-95410, ZINC17378346, tert-Butoxycarbonyl azide [Forbidden], AKOS006229511, Carbonazidic acid,1-dimethylethyl ester, N-diazo-carbamic acid tert-butyl ester, Carbonazidic acid,1,1-dimethylethyl ester, OR039116, OR199101, (NE)-N-diazocarbamic acid tert-butyl ester, Formic acid, azido-, tert-butyl ester (8CI), 113524-EP2281820A2, 113524-EP2298754A1, A801554, 51514-26-2, 69109-90-6

Removed Synonyms

tert-Butylcarbazate, Formic acid, tert-butyl ester, CID61256, A459

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