Triethylamine → HCID 10950276, compound

HRID 2230412Notes

Reaction equation

HRID 2230412 reaction equation
C(OC([NH:11][C@H:12]([C:16](O)=[O:17])[CH:13]([CH3:15])[CH3:14])=O)C1C=CC=CC=1.[NH2:19][C@@H:20]([CH2:54][OH:55])[C@@H:21]([OH:53])[C@@H:22]([OH:52])[C@H:23]([OH:51])[C:24]([NH:26][C@H:27]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:28][C:29]([O:31]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:30])=[O:25].C(N(CC)CC)C>CN(C)C=O.CO.[Pd]>[OH:51][C@@H:23]([C@H:22]([OH:52])[C@H:21]([OH:53])[C@@H:20]([NH:19][C:16](=[O:17])[C@H:12]([CH:13]([CH3:15])[CH3:14])[NH2:11])[CH2:54][OH:55])[C:24]([NH:26][C@H:27]([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[CH2:28][C:29]([OH:31])=[O:30])=[O:25]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 726987N-Carbobenzoxy-L-valineHCID 10864116HCID 10864116, compound

Product 1

HCID 10950276HCID 10950276, compoundYield 152.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-benzyloxycarbonyl-L-valine (460 mg) and diphenylmethyl (S)-3-[(2S,3R,4R,5S)-5-amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionate (500 mg) in dimethylformamide (50 ml) were added diethyl cyanophosophonate (298 mg) and triethylamine (0.191 ml) and the whole was stirred at room temperature for 15 hours. Aftert concentration under reduced pressure, to the residue was added 0.1N hydrochloric acid (50 ml) and the whole was extracted with ethyl acetate (100 ml). The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine respectively and dried over anhydrous sodium sulfate. Removal of the organic solvent gave a residue, which was dissolved in methanol (20 ml) and stirred at room temperature with 10% palladium on activated carbon (150 mg) under hydrogen atmosphere for 1 hour. After filtration, the filtrate was concentrated under reduced pressure to give a residue, which was passed through a column of DIAION HP-20SS (Mitsubishi kasei corporation), followed by elution with water-acetonitrile. The effective fractions were combined and concentrated under reduced pressure. The residue was recrystallized from methanol-ethyl acetate to afford the title compound (663 mg).

Workup

  1. concentrationAftert concentration under reduced pressure
  2. additionto the residue was added 0.1N hydrochloric acid (50 ml)
  3. extractionthe whole was extracted with ethyl acetate (100 ml)
  4. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine respectively
  5. dry with materialdried over anhydrous sodium sulfate
  6. customRemoval of the organic solvent
  7. customgave a residue, which
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customto give a residue, which
  11. washfollowed by elution with water-acetonitrile
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-8c9e2aadd60a422a95ed5ac9e6d55d08
Source dataset
uspto-grants-2002_07
Patent number
US06423869B1

Reaction notes

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