HCID 178418361, compound → HCID 178471568, compound

HRID 1494617Notes

Reaction equation

HRID 1494617 reaction equation
[C:1]([NH:4][C:5]1[N:6]=[C:7]([OH:40])[C:8]2[CH:14]=[C:13]([C:15]([CH3:39])=[CH:16][C:17]3[CH:38]=[CH:37][C:20]([C:21]([NH:23][C@H:24]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:22])=[CH:19][CH:18]=3)[CH:12]=[N:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2].[H][H]>FC(F)(F)C(O)=O.[Pd]>[C:1]([NH:4][C:5]1[N:6]=[C:7]([OH:40])[C:8]2[CH2:14][CH:13]([CH:15]([CH3:39])[CH2:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([NH:23][C@H:24]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:22])=[CH:37][CH:38]=3)[CH2:12][NH:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178471566HCID 178471566, compound

Product 1

HCID 178471568HCID 178471568, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 84.4 mg of diethyl N-(4-[2-(2-acetamido-4-hydroxypyrido[2,3-d]pyrimidin-6-yl)prop-1-enyl]benzoyl)-L-glutamate in 30 mL of trifluoroacetic acid was hydrogenated at 55 psi of hydrogen in the presence of 0.42 g of 5% Pd/C at room temperature for 24 hours. The catalyst was removed by filtration and the filtrate was evaporated under reduced pressure. The resulting residue was taken up in chloroform and was extracted with a saturated sodium bicarbonate solution. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was then subjected to thin layer chromatography using a 5% methanol:chloroform mixture as the eluent. After elution of a first fraction, there was obtained 19.6 mg of the title compound, NMR (CDCl3 250 MHz), d 1.20-1.33(m, overlapping methyls, 9H), 2.45-3.36(m, 15H), 4.11(q, 2H, J=7.14 Hz), 4.23(q, 2H, J=7.10 Hz), 4.89(m, 1H), 5.44(brs, 1H), 7.24(d, 2H, J=7.54 Hz), 7.72(d, 2H, J=7.54 Hz), 9.77(brs, 1H), 11.26(brs, 1H).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated under reduced pressure
  3. extractionwas extracted with a saturated sodium bicarbonate solution
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. washAfter elution of a first fraction

Sources & evidence

ORD record
ord-8d00da79007f4d36aeb40cf97ec44bb8
Source dataset
uspto-grants-1991_06
Patent number
US05026851

Reaction notes

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