Sodium Acetate → HCID 178471576, compound

HRID 2350904Notes

Reaction equation

HRID 2350904 reaction equation
[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:20])[C:11]2[CH:17]=[C:16]([CH:18]=O)[CH:15]=[N:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].Cl.[NH2:22][CH2:23][C:24]1[CH:45]=[CH:44][C:27]([C:28]([NH:30][C@H:31]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:29])=[CH:26][CH:25]=1.C([O-])(=O)C.[Na+]>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:20])[C:11]2[CH:17]=[C:16]([CH2:18][NH:22][CH2:23][C:24]3[CH:25]=[CH:26][C:27]([C:28]([NH:30][C@H:31]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:29])=[CH:44][CH:45]=3)[CH:15]=[N:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 14796054HCID 14796054, compoundHCID 178447257HCID 178447257, compound

Product 1

HCID 178471576HCID 178471576, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 3.0 g (10.9 mmol) of 2-pivaloylamino-4-hydroxy-6-formylpyrido[2,3-d]pyrimidine, 4.47 g of diethyl N-(p-aminomethylbenzoyl)-L-glutamate hydrochloride (12.25 mmol), and 1.0 g (12.25 mmol) of sodium acetate in 70 mL of glacial acetic was stirred at 25° C. for 18 hours. To this solution was added 0.42 g (0.54 mL, 3.65 mmol) of borane-triethylamine complex. This mixture was stirred at 25° C. for 2 hours and the solvent then removed under reduced pressure. The residue was taken up in methylene chloride (200 mL), extracted once with water, and then twice with a saturated aqueous solution of sodium bicarbonate. The aqueous layers were combined and back extracted with methylene chloride. The organic layers were combined, dried over anhydrous magnesium sulfate, and the solvent removed under reduced pressure. The residue was recrystallized from ethyl acetate to give 3.4 g (52% yield) of diethyl N-[N-(2-pivaloylamino-4-hydroxypyrido[2,3-d]pyrimidin-6-ylmethyl)-4-aminomethylbenzoyl]-glutamate; mp 149°-151° C.; 1H NMR (Me2Sod6) delta 1.10-1.17 (m, 6H), 1.22 (s, 9H), 1.9-2.15 (m, 2H), 2.40 (t, 2H, J=7.4 Hz), 3.75 (s, 2H), 3.77 (s, 2H), 3.97-4.10 (m, 4H), 4.36-4.44 (m, 1H), 7.41-7.44 (m, 2H, AA'BB'), 7.80-7.83 (m, 2H, AA'BB'), 8.345 (d, 1H, J=2.09 Hz), 8.65 (d, 1H, J=7.38 Hz), 8.76 (d, 1H, J=2.09 Hz). Anal. Calcd for C30H38N6O7 : C, 60.59; H, 6.44; N, 14.13. Found: C, 60.75; H, 6.68; N, 14.33.

Workup

  1. additionTo this solution was added 0.42 g (0.54 mL, 3.65 mmol) of borane-triethylamine complex
  2. stirringThis mixture was stirred at 25° C. for 2 hours
  3. customthe solvent then removed under reduced pressure
  4. extractionextracted once with water
  5. extractionback extracted with methylene chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent removed under reduced pressure
  8. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ea4b6f082733490a80622841570a357d
Source dataset
uspto-grants-1989_10
Patent number
US04871746

Reaction notes

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