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

HRID 358298ノート

反応式

HRID 358298 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-db579e9412f4450693c8508f08e18ef0
出典データセット
uspto-grants-1984_08
特許番号
US04465844

反応ノート

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