(S)-2-tert-butoxycarbonylaminopropionimidic acid ethyl ester → [(S)-1-((S)-6-Fluoro-3-methyl-3,4-dihydro-5-oxa-1,2a-diazaacenaphthylen-2-yl)ethyl]carbamic acid tert-butyl ester

HRID 243232Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 243232
[F:1][C:2]1[C:11]2[O:10][CH2:9][C@H:8]([CH3:12])[NH:7][C:6]=2[C:5]([NH2:13])=[CH:4][CH:3]=1.C(O[C:17](=N)[C@@H:18]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH3:19])C>CCO>[C:24]([O:23][C:21](=[O:22])[NH:20][C@H:18]([C:17]1[N:7]2[C:6]3[C:11]([O:10][CH2:9][C@@H:8]2[CH3:12])=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[N:13]=1)[CH3:19])([CH3:27])([CH3:26])[CH3:25]

Komponenten

4

Edukt 2

HCID 45092259(S)-2-tert-butoxycarbonylaminopropionimidic acid ethyl esterHCID 68158155(S)-8-Fluoro-3-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-5-ylamine

Produkt 1

HCID 68158968[(S)-1-((S)-6-Fluoro-3-methyl-3,4-dihydro-5-oxa-1,2a-diazaacenaphthylen-2-yl)ethyl]carbamic acid tert-butyl esterAusbeute 76,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

(S)-8-Fluoro-3-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-5-ylamine (160 mg, 0.86 mmol) was added to a solution of (S)-2-tert-butoxycarbonylaminopropionimidic acid ethyl ester (570 mg, 2.64 mmol) in EtOH (10 mL) and the reaction was heated at 75° C. for 60 min. The reaction mixture was concentrated in vacuo, and the residue was partitioned between DCM and sat. NaHCO3. The organic phase was washed with brine, dried (Na2SO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si—PPC, gradient 0-40% DCM in cyclohexane) to afford the title compound as an off-white foam (220 mg, 76%). LCMS (Method J): RT=2.50 min, [M+H]+=336.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between DCM and sat. NaHCO3
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3328744f466141baafb0b12154c8ee98
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653089B2

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