tert-butyl N-hydroxycarbamate → HCID 86654174, compound

HRID 1475995Notes

Reaction equation

HRID 1475995 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:17])[C@@H:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18]([O:22][C:23]([NH:25]O)=[O:24])([CH3:21])([CH3:20])[CH3:19]>>[C:1]([O:5][C:6]([N:8]([CH3:17])[C@@H:9]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:10]([O:12][NH:25][C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:24])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 97534tert-butyl N-hydroxycarbamateHCID 7010555(2S)-2-{[(tert-butoxy)carbonyl](methyl)amino}-4-methylpentanoic acid

Product 1

HCID 86654174HCID 86654174, compound

Procedure

[(tert-Butoxy)carbonyl]amino (2S)-2-{[(tert-butoxy)carbonyl](methyl)amino}-4-methylpentanoate is prepared from (2S)-2-{[(tert-butoxy)carbonyl](methyl)amino}-4-methylpentanoic acid and N-tert-butoxycarbonyl hydroxylamine according to Scheme 6. The compound exists as rotomers and is reported as such. (1.8 g, 58%), 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.49-8.06 (1H, m), 4.75-5.10 (1H, m), 2.86 (3 H, d, 7.8 Hz), 1.66-1.88 (2H, m), 1.54-1.64 (1H, m), 1.50 (9H, s), 1.47 (9H, d, 3.7 Hz), 0.96 (6H, dd, 10.7, 6.6 Hz).

Sources & evidence

ORD record
ord-f4ddd695609d4bf293d3806dc9d9323e
Source dataset
uspto-grants-2015_04
Patent number
US09018411B2

Reaction notes

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