Synthesis of tert-butyl azidoacetate

Preparation of tert-butyl azidoacetate

Preparation of tert-butyl azidoacetate

Preparation of tert-butyl azidoacetate

To 39 g. (0.6 mol.) sodium azide in 150 ml. 60% (v/v) acetone were added 78 g. (0.4 mol.) t-butyl bromoacetate. Two phases were formed. The mixture was refluxed on a steam bath for 14 hours. The acetone was removed through a column. The oil was dissolved in 100 ml. ether and the aqueous phase was extracted several times with two 70-ml. portions of ether. The combined ether solutions were dried over anhydrous sodium sulfate and filtered. The ether was distilled through a column. Fractionation gave 60 g. (95%) tert-butyl azidoacetate, boiling at 79-80.5° C/18 mm.

J. Org. Chem., 1960, 25 (3), pp 387–390

Collect. Czech. Chem. Commun. 1978, 43, 1694.

Org. Synth. 2007, 84, 262.

IUPAC Name

tert-butyl 2-azidoacetate

InChI

InChI=1S/C6H11N3O2/c1-6(2,3)11-5(10)4-8-9-7/h4H2,1-3H3

InChI Key

OUEOSPDVAWGMKX-UHFFFAOYSA-N

Canonical SMILES

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

Depositor-Supplied Synonyms

tert-butyl 2-azidoacetate, tert-butyl azidoacetate, 6367-36-8, CCRIS 8047, T-Butylazidoacetate, T-Butyl azidoacetate, AC1L3S2T, tert-butyl 2-azidoethanoate, SCHEMBL13558775, CTK5B9650, Azidoacetic acid tert-butyl ester, MolPort-013-674-273, OUEOSPDVAWGMKX-UHFFFAOYSA-N, 2-azidoacetic acid tert-butyl ester, AKOS010631915, ZINC100487190, MCULE-6083764240, NE12288, OR313131, FT-0658472, Acetic acid, azido-, 1,1-dimethylethyl ester, Acetic acid, 2-azido-,1,1-dimethylethyl ester, A834462, S14-1035

Removed Synonyms

CID145863

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