Sodium Methoxide → HCID 59344766, compound

HRID 18035Notes

Reaction equation

HRID 18035 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:27])[C:10](=[O:26])[N:11]3[CH2:19][CH:18]([CH2:20][O:21]C(=O)C)[O:17][C:16](=[O:25])[C:12]3=2)[C:7]1=[O:28].C[O-].[Na+]>CO.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:27])[C:10](=[O:26])[N:11]3[CH2:19][CH:18]([CH2:20][OH:21])[O:17][C:16](=[O:25])[C:12]3=2)[C:7]1=[O:28]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 59344754HCID 59344754, compound

Product 1

HCID 59344766HCID 59344766, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 9-(3-chloro-4-fluorobenzyl)-7-hydroxy-3-(acetyloxymethyl)-3,4,10,11-tetrahydro[1,4]oxazino[3,4-a]-2,6-naphthyridine-1,6,8(9H)-trione (46 mg, 0.10 mmol) and 30% sodium methoxide in methanol (39 mg) in dioxane (1.5 mL) was stirred at room temperature for 2 hours. The product mixture was concentrated under vacuum. The residue was dissolved in DMSO and subjected to reverse phase column chromatography on C-18 stationary phase eluted with a 95-5% water-acetonitrile gradient. Collection and lyophilization of appropriate fractions afforded the title compound.

Workup

  1. concentrationThe product mixture was concentrated under vacuum
  2. dissolutionThe residue was dissolved in DMSO
  3. washeluted with a 95-5% water-acetonitrile gradient
  4. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-ad37697c31b54840ace55fe43b2ebc0d
Source dataset
uspto-grants-2010_06
Patent number
US07741315B2

Reaction notes

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