Methanol → 5-[4-((4S,5R)-3-tert-Butoxycarbonyl-4-fluoromethyl-2,2-dimethyl-oxazolidin-5-yl)-phenyl]-pyridine-2-carboxylic acid

HRID 1487515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1487515
[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][F:14])[C@@H:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[N:23][C:24]([C:27]#N)=[CH:25][CH:26]=3)=[CH:17][CH:16]=2)[O:10][C:9]1([CH3:30])[CH3:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-:31].[K+].C[OH:34]>>[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][F:14])[C@@H:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([OH:34])=[O:31])=[N:23][CH:22]=3)=[CH:17][CH:16]=2)[O:10][C:9]1([CH3:30])[CH3:29])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 86695461(4S,5R)-5-[4-(6-Cyano-pyridin-3-yl)-phenyl]-4-fluoromethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Produkt 1

HCID 866954625-[4-((4S,5R)-3-tert-Butoxycarbonyl-4-fluoromethyl-2,2-dimethyl-oxazolidin-5-yl)-phenyl]-pyridine-2-carboxylic acid

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To the solution of (4S,5R)-5-[4-(6-Cyano-pyridin-3-yl)-phenyl]-4-fluoromethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.3 g, 0.729 mmol) in methanol (3 mL) is added KOH (0.409 g, 7.29 mmol) at room temperature. Resulting reaction mixture heated at 65° C. for 48 hours. Solvent is evaporated in vacuo, water (10 mL) is added and aqueous layer is washed with CH2Cl2. Aqueous layer is acidified with saturated citric acid solution and extracted with CH2Cl2. Organic layer dried over sodium sulphate, solvent is evaporated in vacuo to afford title compound (0.22 g): 1H-NMR (400 MHz, DMSO-d6): δ: 1.43 (s, 9H), 1.51 (s, 3H), 1.64 (s, 3H), 3.84-3.90 (m, 2H), 4.45-4.59 (m, 2H), 4.77-5.0 (m, 2H), 5.14 (d, 1H, J=7.2 Hz), 7.61 (d, 2H, J=8.08 Hz), 7.83 (d, 2H, J=8.12 Hz), 8.08 (d, 1H, J=8.32 Hz), 8.23 (d, 1H, J=8.68 Hz), 9.0 (s, 1H). LC-MS (m/z): [M+H]=431.2.

Aufarbeitung

  1. customResulting
  2. customreaction mixture
  3. customSolvent is evaporated in vacuo, water (10 mL)
  4. additionis added
  5. washaqueous layer is washed with CH2Cl2
  6. extractionextracted with CH2Cl2
  7. dry with materialOrganic layer dried over sodium sulphate, solvent
  8. customis evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fdbc149054fc433299f49ec5215652f1
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428528B2

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