Acetyl chloride → (ACETYLOXY)-CARBAMIC ACID TERT-BUTYL ESTER

HRID 1475960Notes

Reaction equation

[C:1](Cl)(=[O:3])[CH3:2].[C:5]([O:9][C:10]([NH:12][OH:13])=[O:11])([CH3:8])([CH3:7])[CH3:6]>>[C:1]([O:13][NH:12][C:10]([O:9][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:11])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 6367Acetyl chloride

HCID 97534tert-butyl N-hydroxycarbamate

Product 1

HCID 10058028(ACETYLOXY)-CARBAMIC ACID TERT-BUTYL ESTER

Procedure

[(tert-Butoxy)carbonyl]amino acetate is prepared from acetyl chloride and N-tert-butoxycarbonyl hydroxylamine according to Scheme 1 and the method described by Carpino et al. J. Am. Chem. Soc. 1959, 955-957. (10 g, 100%), 1H NMR (500 MHz, DMSO-d6) δ ppm 10.57 (1H, br. s.), 2.10 (3H, s), 1.41 (9H, s).

Sources & evidence

ORD record: ord-d05cb9b782534d2183f65ac043b75006
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018411B2

Reaction notes

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