Diisopropylethylamine → (2S,5R)-6-(allyloxy)-2-(methoxymethyl)-N,N-dimethyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-4-carboxamide

HRID 627170Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627170
[CH2:1]([O:4][NH:5][C@@H:6]1[C:11]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])=[CH:10][C@@H:9]([CH2:17][O:18][CH3:19])[NH:8][CH2:7]1)[CH:2]=[CH2:3].CCN(C(C)C)C(C)C.Cl[C:30](Cl)([O:32]C(=O)OC(Cl)(Cl)Cl)Cl>C(#N)C>[CH2:1]([O:4][N:5]1[C:30](=[O:32])[N:8]2[CH2:7][C@H:6]1[C:11]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])=[CH:10][C@H:9]2[CH2:17][O:18][CH3:19])[CH:2]=[CH2:3]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 89852322(3R,6S)-3-(allyloxyamino)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamide2×

Produkt 1

HCID 89852352(2S,5R)-6-(allyloxy)-2-(methoxymethyl)-N,N-dimethyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-4-carboxamideAusbeute 206,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

A solution of (3R,6S)-3-(allyloxyamino)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamide (Intermediate 142, 725 mg, 2.69 mmol) and Hunig's Base (1.880 mL, 10.77 mmol) in acetonitrile (350 mL) was cooled to below 0° C. in an ice-salt bath and then a solution of triphosgene (320 mg, 1.08 mmol) in ACN (22 mL) was added at a rate of 0.1 mL/min. The reaction was stirred overnight at rt. Upon completion of the reaction, the solvents were removed and the crude mixture was redissolved in EtOAc, washed with sat. NaHCO3 and brine, dried over MgSO4, filtered and concentrated to obtain the desired product (658 mg, 83%) as a pale yellow oil.

Aufarbeitung

  1. customUpon completion of the reaction
  2. customthe solvents were removed
  3. dissolutionthe crude mixture was redissolved in EtOAc
  4. washwashed with sat. NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d4551fc08ac84952aed435d11e22faf1
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309245B2

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