Phosgene → 2-{[({[(tert-Butoxy)carbonyl]amino}oxy)carbonyl]oxy}-1,3-diethoxypropane

HRID 1476009Notes

Reaction equation

HRID 1476009 reaction equation
[OH:1][NH:2][C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[CH2:10]([O:12][CH2:13][CH:14]([OH:19])[CH2:15][O:16][CH2:17][CH3:18])[CH3:11].[C:20](Cl)(Cl)=[O:21]>C1(C)C=CC=CC=1>[C:5]([O:4][C:3]([NH:2][O:1][C:20]([O:19][CH:14]([CH2:15][O:16][CH2:17][CH3:18])[CH2:13][O:12][CH2:10][CH3:11])=[O:21])=[O:9])([CH3:8])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 776641,3-Diethoxy-2-propanolHCID 97534tert-butyl N-hydroxycarbamate

Product 1

HCID 866541832-{[({[(tert-Butoxy)carbonyl]amino}oxy)carbonyl]oxy}-1,3-diethoxypropane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-{[({[(tert-Butoxy)carbonyl]amino}oxy)carbonyl]oxy}-1,3-diethoxypropane is prepared from tert-butyl N-hydroxycarbamate and 1,3-diethoxypropan-2-ol using 20% solution of phosgene in toluene according to Scheme 10. (10.37 g, 85%), 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.73 (1H, s), 5.03 (1H, quin, 5.2 Hz), 3.64 (4H, dd, 5.1, 2.7 Hz), 3.48-3.57 (4H, m), 1.50 (9H, s), 1.19 (6H, t, 7.0 Hz).

Sources & evidence

ORD record
ord-96e6f0292a884a2884d4b6f9cae6d922
Source dataset
uspto-grants-2015_04
Patent number
US09018411B2

Reaction notes

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