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

HRID 5098

反応式

HRID 5098 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-33c9f6ab5a574eb69e32dd61abca60bf
出典データセット
uspto-grants-1993_09
特許番号
US05242914

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