Ethanol → HCID 178445755, Verbindung

HRID 1036383

Reaktionsgleichung

Reaktionsgleichung von HRID 1036383
[CH2:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C@:22]2([CH3:28])[CH2:26][O:25]C(=O)[NH:23]2)[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[OH-].[Li+].C(O)C.O>>[NH2:23][C@@:22]([C:17]1[CH:16]=[CH:15][C:14]2[C:19](=[CH:20][CH:21]=[C:12]([O:11][C@H:8]3[CH2:7][CH2:6][C@@H:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:10][CH2:9]3)[CH:13]=2)[CH:18]=1)([CH3:28])[CH2:26][OH:25]

Komponenten

5

Edukt 4

HCID 702EthanolHCID 962WaterHCID 3939Lithium HydroxideHCID 178445732HCID 178445732, Verbindung

Produkt 1

HCID 178445755HCID 178445755, Verbindung

Versuchsvorschrift

The mixture of (R)-4-(6-(cis-4-butylcyclohexyloxy)naphthalen-2-yl)-4-methyloxazolidin-2-one (294.3 mg, 0.7714 mmol) and lithium hydroxide (203 mg, 8.48 mmol) in Ethanol (4.9 mL, 0.084 mol) and water (1.6 mL, 9.1 mmol) was heated to reflux for overnight. LCMS showed reaction completed. The solvent was removed under vacuum and the residue was partitioned between water and CH2Cl2. The aqueous was extensively extracted with CH2Cl2. And the combined organic phase was dried over Na2SO4. The concentrated residue was taken up into CH2Cl2 and subjected to chromatography purification with CH2Cl2/MeOH (10:90 to 80:20) to give the product. LCMS 339.53 ([M−NH2]+, 100%). 1H NMR (400 MHz, CD3OD) δ ppm 0.92 (t, J=7.0 Hz, 3H), 1.21-1.50 (m, 9H), 1.54 (s, 3H), 1.56-1.71 (m, 4H), 2.05 (brd, J=13.3 Hz, 2H), 3.71 (AB, J=10.8 Hz, 2H), 4.69 (brs, 1H), 7.14 (dd, J=8.8, 3.3 Hz, 1H), 7.19 (s, 1H), 7.53 (d, J=8.7 Hz, 1H), 7.72 (d, J=8.7 Hz, 1H), 7.76 (d, J=8.7 Hz, 1H), 7.83 (s, 1H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for overnight
  3. customreaction
  4. customThe solvent was removed under vacuum
  5. customthe residue was partitioned between water and CH2Cl2
  6. extractionThe aqueous was extensively extracted with CH2Cl2
  7. dry with materialAnd the combined organic phase was dried over Na2SO4
  8. customsubjected to chromatography purification with CH2Cl2/MeOH (10:90 to 80:20)
  9. customto give the product

Quellen und Nachweise

ORD-Eintrag
ord-617d8c49d46644f4af29d5a7b0e4b663
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546359B2

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