Sodium Chloride → (2S, 4S)-1-t-Butoxycarbonyl-2-ethylcarbamoyl-4-hydroxypyrrolidine

HRID 5098

반응식

HRID 5098 반응식
ClC(OCC)=O.[C:7]([O:11][C:12]([N:14]1[CH2:18][C@@H:17]([OH:19])[CH2:16][C@H:15]1[C:20]([OH:22])=O)=[O:13])([CH3:10])([CH3:9])[CH3:8].[CH2:23]([NH2:25])[CH3:24].[Cl-].[Na+]>O1CCCC1.C(N(CC)CC)C>[C:7]([O:11][C:12]([N:14]1[CH2:18][C@@H:17]([OH:19])[CH2:16][C@H:15]1[C:20](=[O:22])[NH:25][CH2:23][CH3:24])=[O:13])([CH3:8])([CH3:9])[CH3:10]

참가 물질

7

반응물 4

HCID 5234Sodium ChlorideHCID 6341EthylamineHCID 10928Ethyl chloroformateHCID 688614(2S,4S)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

생성물 1

HCID 57061747(2S, 4S)-1-t-Butoxycarbonyl-2-ethylcarbamoyl-4-hydroxypyrrolidine

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8471Triethylamine용매

실험 절차

15.25 ml of triethylamine and subsequently a solution of 10.48 ml of ethyl chloroformate in 50 ml of dry tetrahydrofuran were added at -25° C. to a solution of 23.13 g of (2S, 4S)-1-t-butoxycarbonyl-4-hydroxy-2-pyrrolidinecarboxylic acid dissolved in 350 ml of dry tetrahydrofuran, and the mixture was stirred at the same temperature for 30 minutes. At the end of this time, a 70% by volume aqueous ethylamine solution was added at -22° C., the reaction temperature was allowed to rise gradually and the reaction finished when the temperature reached 10° C. The reaction mixture was then mixed with a small amount of an aqueous solution of sodium chloride, after which it was extracted thrice with ethyl acetate. The combined extracts were washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, to afford 23.60 g of the title compound as a colorless oil.

후처리

  1. customreached 10° C
  2. extractionafter which it was extracted thrice with ethyl acetate
  3. washThe combined extracts were washed with an aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was then removed by distillation under reduced pressure

출처 및 근거

ORD 기록
ord-33c9f6ab5a574eb69e32dd61abca60bf
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05242914

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