N,O-Dibenzylhydroxylamine → HCID 85435483, compound

HRID 1836459Notes

Reaction equation

HRID 1836459 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][C:5](=[CH:7][C:8](Cl)=[O:9])[C:4](=[O:11])[O:3]1.[CH2:13]([NH:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:13]([N:20]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:8](=[O:9])[CH:7]=[C:5]1[C:4](=[O:11])[O:3][C:2]([CH3:12])([CH3:1])[O:6]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 11063773N,O-DibenzylhydroxylamineHCID 85435482(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride

Product 1

HCID 85435483HCID 85435483, compoundYield 92%

Procedure

Reaction of (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride with N,O-dibenzyl-hydroxylamine (Bhat, J. I., Clegg, W.; Maskill, H.; Elsegood, M. R. J.; Menner, I. D.; Miatt, P. C. J. Chem. Soc. Perkin Trans. 2, 2000, 1435-1446) as described in the preparation of compound 1-A gave the title amide as white crystals (92% yield): mp 107-108° C. (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.72 (6H, s), 4.76 (2H, s), 4.84 (2H, s), 6.36 (1H, s), 7.28-7.38 (10H, m). HRMS (MAB N2) calculated for C21H21NO5[M+]: 367.141973: Found: 367.140292.

Sources & evidence

ORD record
ord-56ca7d9d3a7f4d36808c8a88c88dd32a
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Reaction notes

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