Methyl iodide → (4S)-3-Benzyloxycarbonyl-1-methyl-2-oxoimidazolidine-4-carboxylic acid tert-butyl ester

HRID 1702198ノート

反応式

HRID 1702198 の反応式
[CH2:1]([O:8][C:9]([N:11]1[C@H:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][NH:13][C:12]1=[O:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24]I>CN(C)C=O.C(OCC)(=O)C.[Ag]=O>[CH3:24][N:13]1[CH2:14][C@@H:15]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[C:12]1=[O:23]

参加物

6

反応物 2

HCID 6328Methyl iodideHCID 110671601-benzyl 5-tert-butyl (5S)-2-oxoimidazolidine-1,5-dicarboxylate

生成物 1

HCID 13053974(4S)-3-Benzyloxycarbonyl-1-methyl-2-oxoimidazolidine-4-carboxylic acid tert-butyl ester収率 84.3%

試薬・触媒・溶媒 3

HCID 92152Silver(II) oxide触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

9.6 g of tert.-butyl (4S)-3-benzyloxycarbonyl-2-oxo-imidazolidine-4-carboxylate are dissolved in 200 ml of dimethylformamide, and 14.0 g of silver oxide are added thereto. 42.6 g of methyl iodide are added to the mixture at room temperature under stirring, and the mixture is further stirred for 2 days in the dark. The reaction mixture is filtered to remove insoluble materials, and the filtrate is condensed under reduced pressure. The residue obtained is dissolved in ethyl acetate. Then, the ethyl acetate solution is washed with water, dried and condensed under reduced pressure. The residue thus obtained is washed with n-hexane. 8.45 g of tert.-butyl (4S)-1-methyl-3-benzyloxycarbonyl-2-oxo-imidazolidine-4-carboxylate are thereby obtained as colorless crystals. Yield: 84.3% M.p. 102°-103° C.

後処理

  1. stirringthe mixture is further stirred for 2 days in the dark
  2. filtrationThe reaction mixture is filtered
  3. customto remove insoluble materials
  4. customcondensed under reduced pressure
  5. customThe residue obtained
  6. washThen, the ethyl acetate solution is washed with water
  7. customdried
  8. customcondensed under reduced pressure
  9. customThe residue thus obtained
  10. washis washed with n-hexane

出典と根拠

ORDレコード
ord-9df5057e219e45f7b3de6bd2de2977a4
出典データセット
uspto-grants-1983_04
特許番号
US04380644

反応ノート

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