Acetyl chloride → HCID 10609791, Verbindung

HRID 1968414Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1968414
[C:1]1([C@H:7]2[CH2:11][O:10][C:9](=[O:12])[N:8]2[CH2:13][C:14]([OH:16])=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17](Cl)(=O)C>CO>[C:1]1([C@H:7]2[CH2:11][O:10][C:9](=[O:12])[N:8]2[CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 6367Acetyl chlorideHCID 853681(S)-(+)-2-Oxo-4-phenyl-3-oxazolidineacetic acid

Produkt 1

HCID 10609791HCID 10609791, VerbindungAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of (4(S)-phenyloxazolidin-2-on-3-yl)acetic acid (1 g, 4.52 mmol) (Evans in U.S. Pat. No. 4,665,171) in 20 mL of anhydrous methanol was treated hourly with 5 equivalents of acetyl chloride, for a total of 20 equivalents. The resulting solution was stirred overnight. The residue obtained after evaporation of the MeOH was redissolved in 30 mL of CH2Cl2 and treated with 50 mL of saturated aqueous Na2CO3. The organic layer was evaporated and dried (MgSO4) to yield the title compound as a colorless oil (1.001 g, 94%); 1H NMR (CDCl3) δ 3.37 (d, J=18.0 Hz, 1H), 3.69 (s, 3H), 4.13 (t, J=8.3 Hz, 1H), 4.28 (d, J=18.0 Hz, 1H), 4.69 (t, J=8.8 Hz, 1H), 5.04 (t, J=8.4 Hz, 1H), 7.26-7.29 (m, 2H), 7.36-7.42 (m, 3H).

Aufarbeitung

  1. customThe residue obtained
  2. customafter evaporation of the MeOH
  3. dissolutionwas redissolved in 30 mL of CH2Cl2
  4. additiontreated with 50 mL of saturated aqueous Na2CO3
  5. customThe organic layer was evaporated
  6. dry with materialdried (MgSO4)

Quellen und Nachweise

ORD-Eintrag
ord-aba8c0f4aec44cbf958a02bd636721d9
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426400B2

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