Benzyl chloroformate → Sorbitol

HRID 1078930ノート

反応式

HRID 1078930 の反応式
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]

参加物

4

反応物 3

HCID 10387Benzyl chloroformateHCID 29435DeoxynojirimycinHCID 516892Sodium Bicarbonate

生成物 1

HCID 5780Sorbitol

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-860ec6d7fcad46d192cffc828ba217ed
出典データセット
uspto-grants-1996_08
特許番号
US05550243

反応ノート

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