Sodium Hydroxide → HCID 178525989, compound

HRID 1364379Notes

Reaction equation

HRID 1364379 reaction equation
[CH2:1]([N:8]1[CH:13]=[C:12]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11](=[O:21])[C:10]([C:22](=[O:30])[CH:23]=[C:24]([OH:29])[C:25]([O:27]C)=[O:26])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1>[CH2:1]([N:8]1[CH:13]=[C:12]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:11](=[O:21])[C:10]([C:22](=[O:30])[CH:23]=[C:24]([OH:29])[C:25]([OH:27])=[O:26])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501824HCID 178501824, compound

Product 1

HCID 178525989HCID 178525989, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of methyl-4-(1,5-dibenzyl-1,4-dihydro-4-oxopyridin-3-yl)-2-hydroxy-4-oxobut-2-enoate 15, (0.080 g, 0.19 mmol) and 1 N NaOH (4 mL) in THF (12 mL) was stirred at 0° C. for 4 h. THF was distilled off and the residue acidified with 1 N HCl and extracted with EtOAc (2×25 mL), washed with brine solution (1×25 mL), dried over anhydrous Na2SO4 and EtOAc distilled off to give a yellow solid. The crude solid was triturated with diethylether, filtered and dried under vacuum. Finally the solid was triturated with chloroform, filtered and dried under vacuum for 24 h. Yield 0.065 g (84%), yellow solid, mp 140-142° C. 1H NMR (CDCl3+MeOH-d4, 500 MHz): δ 3.80 (s, 2H, CH2), 4.97 (s, 2H, CH2), 6.95 (t, 1H, CH, J=1 Hz), 7.13-7.40 (m, 11H, Ar—H and olefenic CH), 8.36 (d, 1H, CH, J=2.5 Hz). 13C NMR (CDCl3, 125 MHz): δ 33.4, 61.2, 120.5, 126.5, 127.5, 127.6, 128.6, 128.7, 128.7, 129.1, 129.1, 129.2, 129.2, 129.2, 129.4, 133.8, 135.9, 137.2, 138.2, 143.8, 163.8, 175.4. HRMS (M+H)+ calcd for C23H20NO5 390.1341, found 390.1343.

Workup

  1. distillationTHF was distilled off
  2. extractionextracted with EtOAc (2×25 mL)
  3. washwashed with brine solution (1×25 mL)
  4. dry with materialdried over anhydrous Na2SO4 and EtOAc
  5. distillationdistilled off
  6. customto give a yellow solid
  7. customThe crude solid was triturated with diethylether
  8. filtrationfiltered
  9. customdried under vacuum
  10. customFinally the solid was triturated with chloroform
  11. filtrationfiltered
  12. customdried under vacuum for 24 h

Sources & evidence

ORD record
ord-1314ccc0e18140518414f0c598f329f5
Source dataset
uspto-grants-2011_02
Patent number
US07888375B2

Reaction notes

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