Pivaloyl chloride → [(tert-Butoxy)carbonyl]amino 2,2-dimethylpropanoate

HRID 1475968Notes

Reaction equation

HRID 1475968 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[C:8]([O:12][C:13]([NH:15][OH:16])=[O:14])([CH3:11])([CH3:10])[CH3:9]>>[CH3:1][C:2]([CH3:7])([CH3:6])[C:3]([O:16][NH:15][C:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:14])=[O:4]

Participants

3

Reactant 2

HCID 62493Pivaloyl chlorideHCID 97534tert-butyl N-hydroxycarbamate

Product 1

HCID 300008[(tert-Butoxy)carbonyl]amino 2,2-dimethylpropanoate

Procedure

[(tert-Butoxy)carbonyl]amino 2,2-dimethylpropanoate is prepared from trimethyl acetyl chloride and N-tert-butoxycarbonyl hydroxylamine according to Scheme 1 described by Carpino et al. J. Am. Chem. Soc. 1959, 955-957. (6.4 g, 78%), 1H NMR (250 MHz, DMSO-d6) δ ppm 10.46 (1H, br. s.), 1.40 (9H, s), 1.20 (9H, s).

Sources & evidence

ORD record
ord-f8f5479f001e478ebf05ea4b22f988a3
Source dataset
uspto-grants-2015_04
Patent number
US09018411B2

Reaction notes

Loading…