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

HRID 1980294노트

반응식

HRID 1980294 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 92152Silver(II) oxide촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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 concentrated under reduced pressure. The residue obtained is dissolved in ethyl acetate. Then, the ethyl acetate solution is washed with water, dried and concentrated 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%

후처리

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

출처 및 근거

ORD 기록
ord-75d9220cb3a94842a5a28097d4458f86
출처 데이터셋
uspto-grants-1985_04
특허 번호
US04508727

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