Benzyl chloroformate → Sorbitol

HRID 1078930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1078930
C1N[C@H:5]([CH2:7][OH:8])[C@@H:4]([OH:9])[C@H:3]([OH:10])[C@H:2]1[OH:11].ClC(OCC1C=CC=CC=1)=[O:14].[C:23](=[O:26])(O)[O-].[Na+]>>[CH2:23]([OH:26])[C@@H:7]([C@H:5]([C@@H:4]([C@@H:3]([CH2:2][OH:11])[OH:10])[OH:9])[OH:14])[OH:8]

Komponenten

4

Edukt 3

HCID 10387Benzyl chloroformateHCID 29435DeoxynojirimycinHCID 516892Sodium Bicarbonate

Produkt 1

HCID 5780Sorbitol

Versuchsvorschrift

To a stirred solution of 1-deoxynojirimycin (100 g, 0.61 mol) in saturated aqueous sodium bicarbonate (1000 ml), benzyl chloroformate (95%, 121 g, 0.67 mol) was added dropwise at room temperature. After stirring at room temperature for 18 hr, the solution was extracted once with methylene chloride (300 ml) to remove any unreacted benzyl chloroformate. The aqueous layer was then extracted several times with ethyl acetate to give a total of 2.5-3 liters of the extract. The organic layer was then dried (Na2SO4), filtered and concentrated to give (2) a white solid (98 57 g, 54%), mp 101°-2° C., Anal calcd. for C14H19NO6C, 56.56, H, 6.44, N, 4.71 Found C, 56.33, H, 6.38, N, 4.58., 1H NMR (CD3OD) 7.2-7.4 (m, 5H), 5.15 (s, 2H), 4.23 (br m, 1H), 4.05 (br d., J=8 Hz, 1H), 3.87 (dd, J=6, 4 Hz, 1H), 3.78-3.85 (m, 2H), 3.70-3.78 (m, 2H), 3.45 (br d, J=8 Hz, 1H).

Aufarbeitung

  1. extractionthe solution was extracted once with methylene chloride (300 ml)
  2. customto remove any unreacted benzyl chloroformate
  3. extractionThe aqueous layer was then extracted several times with ethyl acetate
  4. customto give a total of 2.5-3 liters of the extract
  5. dry with materialThe organic layer was then dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-860ec6d7fcad46d192cffc828ba217ed
Quelldatensatz
uspto-grants-1996_08
Patentnummer
US05550243

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