Benzyloxycarbonylglycine → 4-Benzyloxycarbonyl-1,2,3,4-tetrahydropyrazin-2-one

HRID 1840537노트

반응식

HRID 1840537 반응식
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[CH:19](OCC)[CH2:20][NH2:21])C.CCN=C=NCCCN(C)C.Cl>C(#N)C>[CH2:1]([O:8][C:9]([N:11]1[CH:19]=[CH:20][NH:21][C:13](=[O:15])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 14349BenzyloxycarbonylglycineHCID 695242,2-DiethoxyethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 234473834-Benzyloxycarbonyl-1,2,3,4-tetrahydropyrazin-2-one수율 63.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of N-benzyloxycarbonylglycine (10.5 g) and 2,2-diethoxyethylamine (7.33 g) in acetonitrile (50 ml) was added WSC hydrochloride (10.5 g) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated, and to the residue were added ethyl acetate and dilute hydrochloric acid. The organic layer was separated, washed with saturated and saturated brine, dried (MgSO4) and concentrated. To the residue were added p-toluenesulfonic acid (951 mg) and toluene (150 ml), and the mixture was refluxed for 30 minutes. The mixture was cooled, and to the reaction solution was added ethyl acetate. The mixture was washed with saturated sodium bicarbonate solution and saturated brine, dried (MgSO4) and concentrated. The resulting crystals were filtered, washed with ether and dried to give colorless crystals of the title compound (7.37 g).

후처리

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated
  3. additionto the residue were added ethyl acetate and dilute hydrochloric acid
  4. customThe organic layer was separated
  5. washwashed with saturated and saturated brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. additionTo the residue were added p-toluenesulfonic acid (951 mg) and toluene (150 ml)
  9. temperaturethe mixture was refluxed for 30 minutes
  10. temperatureThe mixture was cooled
  11. additionto the reaction solution was added ethyl acetate
  12. washThe mixture was washed with saturated sodium bicarbonate solution and saturated brine
  13. dry with materialdried (MgSO4)
  14. concentrationconcentrated
  15. filtrationThe resulting crystals were filtered
  16. washwashed with ether
  17. customdried

출처 및 근거

ORD 기록
ord-bc543da1ac2c485f8f9a6daca5b9a295
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06680312B2

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