HCID 13518532, compound → HCID 13518534, compound

HRID 370401Notes

Reaction equation

HRID 370401 reaction equation
C([O:8][C:9](=[O:41])[CH2:10][CH2:11][C@H:12]([C:38](=[O:40])[NH2:39])[NH:13][C:14](=[O:37])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[C:29](=[O:30])[C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[C:26](=[O:35])[C:25]=1[CH3:36])C1C=CC=CC=1>CO.O.[Pd]>[CH3:32][O:31][C:28]1[C:29](=[O:30])[C:24]([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:14]([NH:13][C@@H:12]([C:38](=[O:40])[NH2:39])[CH2:11][CH2:10][C:9]([OH:41])=[O:8])=[O:37])=[C:25]([CH3:36])[C:26](=[O:35])[C:27]=1[O:33][CH3:34]

Participants

5

Reactant 1

HCID 13518532HCID 13518532, compound

Product 1

HCID 13518534HCID 13518534, compoundYield 55.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

10-(2,3-Dimethoxy-5-methyl-1,4-benzoquinon-6-yl)decanoyl-D-isoglutamine benzyl ester (3.42 g, 6 mmol) was dissolved in methanol (12 ml) and, the solution was hydrogenated with palladium black at room temperature for 3 hours. After completion of the reaction, the solvent was distilled off and the residue was dissolved in methanol (25 ml). A solution of ferric chloride (2.43 g, 15 mmol) in water (5 ml) was added and the mixture was stirred at room temperature for 10 minutes. The solvent was then distilled off and the residue was dissolved in ethyl acetate (30 ml), washed with water (15 ml×4) and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was chromatographed on a silica gel column. Elution with chloroform-methanol (9:1, v/v), chloroform-acetone-methanol (10:3:2, v/v) and chloroform-methanol-acetic acid (18:2:1, v/v) in that order gave a crude product. The product was recrystallized from ethanol-ethyl ether-petroleum ether to give 10-(2,3-dimethoxy-5-methyl-1,4-benzoquinon-6-yl)decanoyl-D-isoglutamine (1.61 g), melting at 136°-137° C.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionthe residue was dissolved in methanol (25 ml)
  4. distillationThe solvent was then distilled off
  5. dissolutionthe residue was dissolved in ethyl acetate (30 ml)
  6. washwashed with water (15 ml×4)
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was chromatographed on a silica gel column
  10. washElution with chloroform-methanol (9:1
  11. customv/v), chloroform-acetone-methanol (10:3:2, v/v) and chloroform-methanol-acetic acid (18:2:1, v/v) in that order gave a crude product
  12. customThe product was recrystallized from ethanol-ethyl ether-petroleum ether

Sources & evidence

ORD record
ord-617b4c0a1ea840429f54523d9678d6e1
Source dataset
uspto-grants-1985_07
Patent number
US04526719

Reaction notes

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