Pyridine → (S)-Benzyl 2-(2-oxooxazolidin-4-YL)acetate

HRID 2217291

반응식

HRID 2217291 반응식
C(O[C:6]([NH:8][C@H:9]([CH2:21][OH:22])[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:7])(C)(C)C.N1C=CC=CC=1.C1(C)C=CC(S(OS(C2C=CC(C)=CC=2)(=O)=O)(=O)=O)=CC=1>ClC(Cl)C.ClCCl>[O:7]=[C:6]1[NH:8][C@@H:9]([CH2:10][C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])[CH2:21][O:22]1

참가 물질

6

반응물 3

HCID 1049PyridineHCID 77773Toluene-p-sulphonic anhydrideHCID 10040985Phenylmethyl (3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-hydroxybutanoate

생성물 1

HCID 11241814(S)-Benzyl 2-(2-oxooxazolidin-4-YL)acetate

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 63651,1-Dichloroethane용매

반응 조건

온도
2.5 °C

실험 절차

To a solution of the alcohol (95.7 g) from Step 1 in dichloroethane (925 mL) was added pyridine (625 mL) and the mixture was cooled to 0-5° C. Anhydrous p-toluenesulfonic anhydride (105.7 g) was added and the mixture was warmed to room temperature and stirred for 1 hour and then heated to 90° C. for 2 hours. The mixture was cooled, diluted with dichloromethane (1000 mL) and washed with 1N HCl (3×600 mL). The organic layer was washed with brine, dried with sodium sulfate and the solvents were removed in vacuo. The residue was purified by chromatography on SiO2 using ethyl acetate and hexanes in a 1:1 ratio followed by ethyl acetate to yield benzyl [(4S)-2-oxo-1,3-oxazolidin-4-yl]acetate.

후처리

  1. temperaturethe mixture was warmed to room temperature
  2. temperatureheated to 90° C. for 2 hours
  3. temperatureThe mixture was cooled
  4. washwashed with 1N HCl (3×600 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried with sodium sulfate
  7. customthe solvents were removed in vacuo
  8. customThe residue was purified by chromatography on SiO2

출처 및 근거

ORD 기록
ord-5729e5a9a1a640beba3d676e7d3dd832
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07407959B2

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