Benzyl chloroformate → Benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine

HRID 1903599노트

반응식

HRID 1903599 반응식
[O:1]=[C:2]1[CH:6]([CH:7]([C:9]([OH:11])=[O:10])[NH2:8])[CH2:5][C:4](=[O:12])[NH:3]1.[OH-].[Na+].[CH2:15]([O:22][C:23](Cl)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])O.[Na+]>O.O1CCOCC1>[CH2:15]([O:22][C:23]([NH:8][CH:7]([CH:6]1[CH2:5][C:4](=[O:12])[NH:3][C:2]1=[O:1])[C:9]([OH:11])=[O:10])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

6

반응물 4

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 130894332-(2,5-Dioxopyrrolidin-3-yl)glycine

생성물 1

HCID 13105388Benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine

시약·촉매·용매 1

HCID 218864351,4-Dioxane--water (1/1)용매

실험 절차

In 250 ml of water-dioxane (1:1) was suspended 10 g of 2-(2,5-dioxopyrrolidin-3-yl)glycine and under cooling at 0°-5° C. the above amino acid was dissolved by addition of 70 ml of 1 N sodium hydroxide. To this solution was added 15 ml of benzyloxycarbonyl chloride and, with adjusting pH to 7.1-7.4 with sodium hydrogen carbonate, the mixture was stirred at the same temperature as above for 2 hours. The reaction mixture was concentrated under reduced pressure to remove the organic solvent and the concentrate was washed with ethyl acetate. The aqueous layer was adjusted to pH 1 with conc. hydrochloric acid and allowed to stand in a refrigerator overnight to give crystals. Yield 15.8 g.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto remove the organic solvent
  3. washthe concentrate was washed with ethyl acetate
  4. customto stand in a refrigerator overnight
  5. customto give crystals

출처 및 근거

ORD 기록
ord-e4d12ecafb28404cb056b858859da1a8
출처 데이터셋
uspto-grants-1984_03
특허 번호
US04436918

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