Sodium Methoxide → HCID 178490769, compound

HRID 1817347Notes

Reaction equation

HRID 1817347 reaction equation
C([O:4][C:5]1[N:6]=[C:7]([C:27]([N:29]([CH3:31])[CH3:30])=[O:28])[C:8]2[CH2:9][CH2:10][N:11]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[C:12](=[O:17])[C:13]=2[C:14]=1[O:15][CH3:16])(=O)C.C[O-].[Na+]>CO>[OH:4][C:5]1[N:6]=[C:7]([C:27]([N:29]([CH3:31])[CH3:30])=[O:28])[C:8]2[CH2:9][CH2:10][N:11]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[C:12](=[O:17])[C:13]=2[C:14]=1[O:15][CH3:16]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 690652291-[(Dimethylamino)carbonyl]-4-methoxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-3-yl acetate

Product 1

HCID 178490769HCID 178490769, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1-[(dimethylamino)carbonyl]-4-methoxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-3-yl acetate (7.55 g) was dissolved in 50 mL MeOH and treated with 6.65 mL of a 30% by weight solution of NaOMe in MeOH at room temperature for 30 minutes. The reaction was concentrated and the remaining solid partitioned between 10% KHSO4 and chloroform. The organic layer was washed with brine, dried over Na2SO4, and then concentrated to pure product by HPLC/MS and NMR.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe remaining solid partitioned between 10% KHSO4 and chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to pure product by HPLC/MS and NMR

Sources & evidence

ORD record
ord-db948fa0fa4d4fe69b5192f80ff287af
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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