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

HRID 2186125ノート

反応式

HRID 2186125 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-77703b0c0f1245a29a949d2982e7f693
出典データセット
uspto-grants-2002_06
特許番号
US06403595B1

反応ノート

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