Ammonia → HCID 58109425, Verbindung

HRID 2037533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2037533
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([N:17]2[CH2:22][CH2:21][C@@:20]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)([CH2:23][CH2:24][OH:25])[O:19][C:18]2=[O:33])[CH3:16])=[CH:11][CH:10]=1.[C:34](Cl)(=[O:45])OC1C=CC([N+]([O-])=O)=CC=1.[NH3:47]>C(Cl)Cl>[C:34](=[O:45])([O:25][CH2:24][CH2:23][C@@:20]1([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[O:19][C:18](=[O:33])[N:17]([C@H:15]([C:12]2[CH:13]=[CH:14][C:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])=[CH:10][CH:11]=2)[CH3:16])[CH2:22][CH2:21]1)[NH2:47]

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 821294-Nitrophenyl chloroformateHCID 53361128HCID 53361128, Verbindung

Produkt 1

HCID 58109425HCID 58109425, VerbindungAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(S)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one (50 mg, 0.11 mmol) was dissolved in CH2Cl2 (3 mL), followed by the addition of TEA (1 mL) and 4-nitrophenyl carbonochloridate (88 mg, 0.44 mmol). The mixture was stirred at rt overnight. Aqueous ammonia (2 mL) was added and the mixture was stirred at rt for 3 h. After separation of the water layer, the organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo to give the crude product, which was purified by preparative TLC to afford 2-((S)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethyl carbamate (20 mg, 35%). LC-MS Method 3 tR=1.36, min, m/z=499; 1H NMR (CDCl3): 1.48 (m, 3H), 2.14-2.33 (m, 5H), 2.91 (m, 1H), 3.42 (s, 1H), 3.95 (m, 1H), 4.07 (m, 1H), 4.62 (s, 2H), 5.61 (m, 1H), 6.79-7.01 (m, 6H), 7.23 (m, 5H).

Aufarbeitung

  1. stirringthe mixture was stirred at rt for 3 h
  2. customAfter separation of the water layer
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give the crude product, which
  7. customwas purified by preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-963c0d976b854e4ea8f867d4cbfbd9ca
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575156B2

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