Pyridine → HCID 131735503, compound

HRID 521713Notes

Reaction equation

[CH2:1]([N:4]([CH2:12][C:13](=O)[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=[CH2:3].Cl.[NH2:22][OH:23].N1C=CC=CC=1>C(O)C>[CH2:1]([N:4]([CH2:12][C:13](=[N:22][OH:23])[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 80 °C

Procedure

tert-Butyl N-allyl-N-[2-oxo-2-(3-pyridyl)ethyl]carbamate (31.34 g 113.41 mmol) is dissolved in ethanol (110 mL) with stirring under nitrogen. Hydroxylamine hydrochloride (18.31 g, 260.85 mmol) and pyridine (12.84 mL, 158.78 mmol) are added. The resulting solution is heated at 80° C. under nitrogen for 2 hours and then is cooled to room temperature. The solvents are partially evaporated and the resulting residue is then partitioned between 2 M sodium hydroxide (150 ml) and dichloromethane (500 mL). The phases are separated and the aqueous phase is re-extracted with dichloromethane (2×250 mL). The organic extracts are combined and evaporated under reduced pressure. The crude product is purified by silica gel column chromatography using a gradient of 0-10% 0.14 M ammonia/methanol solution in dichloromethane to give the title compound (30.34 g, 91.82%) as a mixture of E/Z isomers. ES/MS (m/e) M+1=292.

Workup

temperatureis cooled to room temperature
customThe solvents are partially evaporated
customthe resulting residue is then partitioned between 2 M sodium hydroxide (150 ml) and dichloromethane (500 mL)
customThe phases are separated
extractionthe aqueous phase is re-extracted with dichloromethane (2×250 mL)
customevaporated under reduced pressure
customThe crude product is purified by silica gel column chromatography

Sources & evidence

ORD record: ord-cb75999696254ceaa796c9b23e3c8e7e
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328124B2

Reaction notes

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