Methylamine → (5R)-3-(3-Ethyl-4-fluoro-2-oxo-2,3-dihydro-6-benzoxazolyl)-N-methyl-2-oxo-5-oxazolidinecarboxamide

HRID 723940Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 723940
[CH3:1][NH2:2].[CH2:3]([N:5]1[C:9]2[C:10]([F:24])=[CH:11][C:12]([N:14]3[CH2:18][C@H:17]([C:19]([O:21]C)=O)[O:16][C:15]3=[O:23])=[CH:13][C:8]=2[O:7][C:6]1=[O:25])[CH3:4]>CO>[CH2:3]([N:5]1[C:9]2[C:10]([F:24])=[CH:11][C:12]([N:14]3[CH2:18][C@H:17]([C:19]([NH:2][CH3:1])=[O:21])[O:16][C:15]3=[O:23])=[CH:13][C:8]=2[O:7][C:6]1=[O:25])[CH3:4]

Komponenten

4

Edukt 2

HCID 6329MethylamineHCID 68490621methyl(5R)-3-(3-ethyl-4-fluoro-2-oxo-2,3-dihydro-6-benzoxazolyl)-2-oxo-5-oxazolidinecarboxylate

Produkt 1

HCID 10125745(5R)-3-(3-Ethyl-4-fluoro-2-oxo-2,3-dihydro-6-benzoxazolyl)-N-methyl-2-oxo-5-oxazolidinecarboxamideAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of methylamine in methanol (2M, 5 ml) is added to solid methyl (5R)-3-(3-ethyl-4-fluoro-2-oxo-2,3-dihydro-6-benzoxazolyl)-2-oxo-5-oxazolidinecarboxylate (EXAMPLE 87, Step 4, 0.250 g, 0.771 mmol) and the suspension stirred overnight at room temperature. The reaction mixture is concentrated under reduced pressure and the residue purified by PTLC (10% methanol/dichloromethane) to give product as a white solid (0.10 g, 40%); MS for C14H14FN3O5 m/z 324 (M+H)+; 1H NMR (DMSO-d6, 300 Mhz) δ 8.40 (m, 1H), 7.51 (d, 1H), 7.44 (dd, 1H), 5.07 (dd, 1H), 4.27 (t, 1H), 4.02 (dd, 1H), 3.85 (q, 2H), 2.65 (d, 3H), 1.28 (t, 3H).

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe residue purified by PTLC (10% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-24e343d158a34901bc5fede866feca20
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141588B2

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