Sodium Sulfate → HCID 57539220, Verbindung

HRID 2096907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2096907
[CH2:1]([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]([CH2:14][OH:15])[C:10]([O:12][CH3:13])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].[F:30][C:31]([F:39])(S(F)(=O)=O)C(O)=O>C(#N)C>[CH2:16]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:9]([CH2:14][O:15][CH:31]([F:39])[F:30])[C:10]([O:12][CH3:13])=[O:11])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

5

Edukt 3

HCID 24436Sodium SulfateHCID 27375162,2-Difluoro-2-(fluorosulfonyl)acetic acidHCID 4184069Methyl 2-(dibenzylamino)-3-hydroxypropanoate

Produkt 1

HCID 57539220HCID 57539220, VerbindungAusbeute 4,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To an acetonitrile solution of methyl 2-(dibenzylamino)-3-hydroxypropanoate (23 g, 76.8 mmol) and sodium sulfate (3.9 g, 27.4 mmol) at 40° C., difluoro(fluorosulfonyl)acetic acid (25 g, 140 mmol) was added dropwise for 1.5 hrs. The reaction mixture was concentrated to dryness and the residue was mixed with silica gel in ethyl acetate, then again concentrated to dryness. The product was purified by column chromatography, eluting with 3-4% ethyl acetate in hexanes, to give methyl 2-dibenzylamino-3-difluoromethoxy-propionate (1.3 g, 4.8%) as a colorless oil. 1H NMR (300 MHz, CDCl3): δ(ppm) 7.20-7.40 (m, 10H), 6.18 (bt, 1H), 4.05-4.24 (m, 2H), 3.90 (d, 2H), 3.83 (s, 3H) and 3.64-3.71 (m, 3H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated to dryness
  2. additionthe residue was mixed with silica gel in ethyl acetate
  3. concentrationagain concentrated to dryness
  4. customThe product was purified by column chromatography
  5. washeluting with 3-4% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-d02e895aa51f4b2c96941b3d92172af3
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450336B2

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