HCID 178418361, compound → HCID 178471556, compound

HRID 231300Notes

Reaction equation

HRID 231300 reaction equation
[C:1]([NH:4][C:5]1[N:6]=[C:7]([OH:39])[C:8]2[CH:14]=[C:13]([CH:15]=[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:39])[C:8]2[CH:14]=[C:13]([CH2:15][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)[CH:12]=[N:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178471555HCID 178471555, compound

Product 1

HCID 178471556HCID 178471556, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of diethyl N-(4-[2-(2-acetamido-4-hydroxypyrido[2,3-d]pyrimidin-6-yl)ethenyl]benzoyl)-L-glutamate in 30 mL of trifluoroacetic acid was hydrogenated at 55 psi of hydrogen in the presence of 1.0 g of 5% Pd/C at room temperature for 14 hours. The catalyst was removed by filtration, the filtrate evaporated under reduced pressure, and the residual solid partitioned between 100 mL of chloroform and 50 ml of 2N aqueous sodium carbonate. The organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent removed by evaporation to give a gum which was chromatographed on silica gel. Elution with chloroform:methanol (97:3) gave 0.25 g (56%) of diethyl N-(4-[2-(2-acetamido-4-hydroxypyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoyl)-L-glutamate; mp 215°-217° C.; NMR (CDCl3) delta 1.25, 1.35 (2t, 6H, J=6 Hz), 2.1-2.5 (m, 4H), 2.55 (s, 3H), 3.1 (s, 4H), 4.15, 4.25 (2q, 4H, J=6 Hz), 4.6-4.96 (m, 1H), 7.05 (s, 1H), 7.25, 7.75 (AB q, 4H, J= 9 Hz), 8.35 (d, 1H, J=3 Hz), 8.77 (d, 1H, J=3 Hz); IR (Nujol) 3200, 3150, 1725, 1675, 1630, 1605 cm-1. Anal.: Calc'd. for C27H31N5O7 : C, 60.32; H, 5.81; N, 13.03. Found: C, 59.98; H, 6.03; N, 12.92).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated under reduced pressure
  3. customthe residual solid partitioned between 100 mL of chloroform and 50 ml of 2N aqueous sodium carbonate
  4. customThe organic phase was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent removed by evaporation
  7. customto give a gum which
  8. customwas chromatographed on silica gel
  9. washElution with chloroform:methanol (97:3)

Sources & evidence

ORD record
ord-dda79f680de9401086bc0454d857e284
Source dataset
uspto-grants-1989_07
Patent number
US04845216

Reaction notes

Loading…