4'-Hydroxyacetophenone → 4-acetylphenyl 3-tert-butoxycarbonyl-2,2-dimethyloxazolidine-4-(R)-carboxylate

HRID 1724721노트

반응식

HRID 1724721 반응식
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]([OH:15])=[O:14])[CH2:11][O:10][C:9]1([CH3:17])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C.O[C:43]1[CH:48]=[CH:47][C:46]([C:49](=[O:51])[CH3:50])=[CH:45][CH:44]=1>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]([O:15][C:43]2[CH:48]=[CH:47][C:46]([C:49](=[O:51])[CH3:50])=[CH:45][CH:44]=2)=[O:14])[CH2:11][O:10][C:9]1([CH3:17])[CH3:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 74694'-HydroxyacetophenoneHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 6932185(R)-3-(Tert-butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid

생성물 1

HCID 690818704-acetylphenyl 3-tert-butoxycarbonyl-2,2-dimethyloxazolidine-4-(R)-carboxylate수율 63.4%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

At 0° C., 3-tert-butoxycarbonyl-2,2-dimethyloxazolidine-4-(R)-carboxylic acid (1.0 g) is dissolved in ethyl acetate (25 ml), dicyclohexylcarbodiimide (DCC; 1.26 g) is then added and the reaction mixture is subjected to agitation for 45 minutes at 0° C. Dimethylaminopyridine (DMAP; 100 mg) and 4′-hydroxyacetophenone (565 mg) are successively added, the reaction mixture is then left to return to room temperature. After 5 hours of agitation, the mixture is filtered and the filtrate is washed with a sodium hydrogen carbonate saturated solution, then with a sodium chloride saturated solution. The organic phase is dried on MgSO4, filtered and concentrated. The obtained orange oil is purified by chromatography on silica to obtain the desired product as a transparent oil (940 mg).

후처리

  1. waitthe reaction mixture is then left
  2. customto return to room temperature
  3. waitAfter 5 hours of agitation
  4. filtrationthe mixture is filtered
  5. washthe filtrate is washed with a sodium hydrogen carbonate saturated solution
  6. customThe organic phase is dried on MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe obtained orange oil is purified by chromatography on silica

출처 및 근거

ORD 기록
ord-f7a900afe54647e698a35ba0b75d4dfd
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07488755B2

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