Dichloromethane → (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl acetate

HRID 1505577

반응식

HRID 1505577 반응식
P([O-])(O)(O)=O.[Na+].C(=O)(O)[O-].[Na+].[C:12]([O:15][CH:16]1[CH:23]2[CH:19]([O:20][CH2:21][CH2:22]2)[O:18][CH2:17]1)(=[O:14])[CH3:13].C(Cl)Cl>O>[C:12]([O:15][C@@H:16]1[C@H:23]2[C@H:19]([O:20][CH2:21][CH2:22]2)[O:18][CH2:17]1)(=[O:14])[CH3:13]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 21869022Hexahydrofuro[2,3-b]furan-3-yl acetateHCID 23672064Monosodium phosphate

생성물 1

HCID 59959307(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl acetate수율 34.8%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
41.5 °C

실험 절차

To the buffer solution (104.3 g of sodium dihydrogen orthophosphate dissolved in 530 mL of water & pH adjusted to 6.0-6.5 with saturated sodium bicarbonate solution (68 g in 680 mL water) solution) hexahydrofuro[2,3-b]furan-3-yl acetate (III, 115 g) and CAL-B (17.25 g) was added at 25-35° C., heated to 38-45° C. and stirred for 24 hours. CAL-B (17.25 g) was added stirred for 16 hours, again CAL-B (11.5 g) was added at 38-45° C. and stirred for 16 hours (pH should maintain 6.0-6.5). The reaction mass was cooled to 20-30° C., methylenedichloride (1150 mL) was added to the mass and stirred for 30 minutes. The reaction mass was filtered through hyflowbed then separated the organic layer and washed with 10% sodium chloride solution (575 mL). Organic layer was distilled completely under vacuum to get title compound II (yield 40.0 g).

후처리

  1. additionwas added at 25-35° C.
  2. additionCAL-B (17.25 g) was added
  3. stirringstirred for 16 hours
  4. additionagain CAL-B (11.5 g) was added at 38-45° C.
  5. stirringstirred for 16 hours
  6. temperature(pH should maintain 6.0-6.5)
  7. temperatureThe reaction mass was cooled to 20-30° C.
  8. stirringstirred for 30 minutes
  9. filtrationThe reaction mass was filtered
  10. customthrough hyflowbed then separated the organic layer
  11. washwashed with 10% sodium chloride solution (575 mL)
  12. distillationOrganic layer was distilled completely under vacuum

출처 및 근거

ORD 기록
ord-339df309fb8d419782686a04b83487bf
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216990B2

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