Triethylamine → N-[3-[4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-ylmethyl)phenyl]propionyl]thiomorpholine

HRID 496334노트

반응식

HRID 496334 반응식
[CH3:1][O:2][C:3]1[C:4](=[O:25])[C:5]([CH3:24])=[C:6]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21](O)=[O:22])=[CH:15][CH:14]=2)[C:7](=[O:11])[C:8]=1[O:9][CH3:10].C(Cl)(=O)OCC.C(N(CC)CC)C.[NH:39]1[CH2:44][CH2:43][S:42][CH2:41][CH2:40]1>C1COCC1.O>[CH3:1][O:2][C:3]1[C:4](=[O:25])[C:5]([CH3:24])=[C:6]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([N:39]3[CH2:44][CH2:43][S:42][CH2:41][CH2:40]3)=[O:22])=[CH:15][CH:14]=2)[C:7](=[O:11])[C:8]=1[O:9][CH3:10]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 67164ThiomorpholineHCID 98410613-[4-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-ylmethyl)phenyl]propionic acid

생성물 1

HCID 9867304N-[3-[4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-ylmethyl)phenyl]propionyl]thiomorpholine수율 78.2%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-[4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-ylmethyl)phenyl]propionic acid (27 mg, 0.078 mmol) obtained in Example 1 and ethyl chlorocarbonate (15 mg, 0.139 mmol) in THF (10 ml) was added triethylamine (14 mg, 0.139 mmol) at −10° C. followed by stirring for 30 minutes, and then thiomorpholine (20 mg, 0.194 mmol) was added thereto followed by stirring at room temperature for 1 hour. The reaction mixture was diluted with water and extracted with ether. The extract was washed with water, dried, and then the solvent was distilled off. The resulting residue was purified by a middle-pressure column chromatography using silica gel (hexane:ethyl acetate=1:1). The yellow powder thus obtained was crystallized from methylene chloride-diethylether to yield the title compound (26 mg, 0.061 mmol, yield 77%) as a yellow crystal.

후처리

  1. stirringby stirring at room temperature for 1 hour
  2. extractionextracted with ether
  3. washThe extract was washed with water
  4. customdried
  5. distillationthe solvent was distilled off
  6. customThe resulting residue was purified by a middle-pressure column chromatography
  7. customThe yellow powder thus obtained
  8. customwas crystallized from methylene chloride-diethylether

출처 및 근거

ORD 기록
ord-6c78b00c149b40d9ad378203c8a60459
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06943196B1

반응 노트

불러오는 중…