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

HRID 496334Notes

Reaction equation

HRID 496334 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6c78b00c149b40d9ad378203c8a60459
Source dataset
uspto-grants-2005_09
Patent number
US06943196B1

Reaction notes

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