L-Serine → N-(Benzyloxycarbonyl)-L-serine

HRID 53357

반응식

HRID 53357 반응식
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].[OH-].[Na+].Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]>O>[C:11]([NH:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4])([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]

참가 물질

5

반응물 3

HCID 5951L-SerineHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2회

생성물 1

HCID 100310N-(Benzyloxycarbonyl)-L-serine

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
25 °C

실험 절차

L-Serine (20.00 g, 190.3 mmol) was dissolved in water, and aqueous sodium hydroxide was added to adjust the pH of the solution to about 8.5 while maintaining the temperature at about 25° C. Benzyl chloroformate (36.0 g, 211.0 mmol) was added while the pH was maintained between 8.3 and 8.5 by the addition of aqueous sodium hydroxide and the temperature was maintained at about 30° C. The mixture was stirred for about 2 hours. The reaction mixture was extracted with methylene chloride. The phases were separated, and the pH of the aqueous phase was adjusted to about 7 with concentrated hydrochloric acid. The aqueous phase was heated to about 40° C. under low vacuum to remove any residual methylene chloride. Water was added and the aqueous solution was heated to about 60° C. The pH was adjusted to about 2 with concentrated hydrochloric acid while maintaining the temperature at about 60° C. The solution was cooled to about 50° C. while stirring and seed crystals were added. With stirring, cooling was continued to about 0° C. to complete the crystallization. The product was collected and the cake was washed with cold (about 5° C.) water. The product was dried under vacuum at about 40° C. to afford carbobenzyloxy-L-serine.

후처리

  1. temperaturethe temperature was maintained at about 30° C
  2. extractionThe reaction mixture was extracted with methylene chloride
  3. customThe phases were separated
  4. temperatureThe aqueous phase was heated to about 40° C. under low vacuum
  5. customto remove any residual methylene chloride
  6. additionWater was added
  7. temperaturethe aqueous solution was heated to about 60° C
  8. temperaturewhile maintaining the temperature at about 60° C
  9. temperatureThe solution was cooled to about 50° C.
  10. stirringwhile stirring
  11. additionseed crystals were added
  12. stirringWith stirring
  13. temperaturecooling
  14. customwas continued to about 0° C.
  15. customthe crystallization
  16. customThe product was collected
  17. washthe cake was washed with cold (about 5° C.) water
  18. customThe product was dried under vacuum at about 40° C.

출처 및 근거

ORD 기록
ord-52ea8117c82a48b084a0887ae07c631a
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618946

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