Diisopropylethylamine → (2S,5R)-6-(allyloxy)-3-ethyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide

HRID 627227Notes

Reaction equation

[CH2:1]([O:4][NH:5][CH:6]1[CH2:11][NH:10][C@@H:9]([C:12]([NH2:14])=[O:13])[C:8]([CH2:15][CH3:16])=[CH:7]1)[CH:2]=[CH2:3].C(N(C(C)C)CC)(C)C.Cl[C:27](Cl)([O:29]C(=O)OC(Cl)(Cl)Cl)Cl>C(#N)C.C(OCC)(=O)C>[CH2:1]([O:4][N:5]1[C:27](=[O:29])[N:10]2[CH2:11][C@H:6]1[CH:7]=[C:8]([CH2:15][CH3:16])[C@H:9]2[C:12]([NH2:14])=[O:13])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (R)-5-(allyloxyamino)-3-ethyl-1,2,5,6-tetrahydropyridine-2-carboxamide (Intermediate 214, 0.35 g, 1.55 mmol) and diisopropylethyl amine (1.082 mL, 6.21 mmol) in acetonitrile (110 mL) at 0° C. was added triphosgene (0.157 g, 0.53 mmol) as a solution in acetonitrile (4 mL). The triphosgene solution was added at a rate of 4 mL/hour. Once addition was complete the reaction was stirred at 0° C. for ˜1 hour. The reaction mixture was diluted with ethyl acetate, then washed with saturated sodium bicarbonate and brine. The aqueous washes were extracted once with dichloromethane. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-100% ethyl acetate/hexanes) afforded the title compound (0.340 g, 87%) as a colorless oil.

Workup

additionOnce addition
washwashed with saturated sodium bicarbonate and brine
extractionThe aqueous washes were extracted once with dichloromethane
dry with materialThe combined organic extracts were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-ff572deaaf354ddc96446791725c2236
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309245B2

Reaction notes

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