Sodium Methoxide → HCID 59344766, compound

HRID 2426490Notes

Reaction equation

HRID 2426490 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-3f95e314795c44ba92691a1a3263ba38
Source dataset
uspto-grants-2011_06
Patent number
US07968564B2

Reaction notes

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