Benzyl chloroformate → Sorbitol

HRID 1078930노트

반응식

HRID 1078930 반응식
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]

참가 물질

4

반응물 3

HCID 10387Benzyl chloroformateHCID 29435DeoxynojirimycinHCID 516892Sodium Bicarbonate

생성물 1

HCID 5780Sorbitol

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-860ec6d7fcad46d192cffc828ba217ed
출처 데이터셋
uspto-grants-1996_08
특허 번호
US05550243

반응 노트

불러오는 중…