Sodium Methoxide → HCID 25083646, compound

HRID 2120283Notes

Reaction equation

HRID 2120283 reaction equation
[C@@H:1]12[CH2:10][C@@H:5]([CH2:6][C:7](=[O:9])[NH:8]1)[CH2:4][CH2:3][C@@H:2]2[N:11]1[CH:19]=[N:18][C:17]2[C:12]1=[N:13][CH:14]=[N:15][C:16]=2[NH:20]C(=O)C1C=CC=CC=1.C[O-].[Na+]>CO>[C@@H:1]12[CH2:10][C@@H:5]([CH2:6][C:7](=[O:9])[NH:8]1)[CH2:4][CH2:3][C@@H:2]2[N:11]1[CH:19]=[N:18][C:17]2[C:12]1=[N:13][CH:14]=[N:15][C:16]=2[NH2:20]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 69217259HCID 69217259, compound2×

Product 1

HCID 25083646HCID 25083646, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 500 ml round-bottomed flask was loaded with 8.2 g of benzoyl-A lactam 15a (22 mmol) and 250 ml of dry methanol. The suspension was heated until 15a had completely dissolved. A solution of 1.62 g of NaOMe in 5.5 l of MeOH was then added and the mixture was stirred at room temperature for 19 h. The resulting suspension was filtered and the precipitate was washed with Et2O. The filtrate was neutralized by addition of ion-exchange resin (Amberlite IR-120, H+ form). The resin was filtered off and the solvent was removed under reduced pressure. The residue was dissolved in 4 ml of MeOH and precipitated by addition of 30 ml of Et2O. The precipitate was filtered and the combined precipitates were dried in vacuo to afford 5.8 g of 15b (21 mmol, 97%), which was sufficiently pure for further reactions. An analytical sample was obtained by crystallization from MeOH/H2O.

Workup

  1. dissolutionhad completely dissolved
  2. filtrationThe resulting suspension was filtered
  3. washthe precipitate was washed with Et2O
  4. additionThe filtrate was neutralized by addition of ion-exchange resin (Amberlite IR-120, H+ form)
  5. filtrationThe resin was filtered off
  6. customthe solvent was removed under reduced pressure
  7. dissolutionThe residue was dissolved in 4 ml of MeOH
  8. customprecipitated by addition of 30 ml of Et2O
  9. filtrationThe precipitate was filtered
  10. customthe combined precipitates
  11. customwere dried in vacuo

Sources & evidence

ORD record
ord-51838b686c1b4c0e9b035b93543095c5
Source dataset
uspto-grants-2004_02
Patent number
US06689884B1

Reaction notes

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