Sodium Methoxide → HCID 58866159, compound

HRID 1354290Notes

Reaction equation

HRID 1354290 reaction equation
[CH2:1]([O:8][NH:9][C:10]([C@H:12]1[C@H:17]2[O:18][C:19]([CH3:22])([CH3:21])[O:20][C@@H:16]2[C@H:15]([O:23]C(=O)C)[CH2:14][N:13]1[S:27]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)(=[O:29])=[O:28])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+]>CO>[CH2:1]([O:8][NH:9][C:10]([C@H:12]1[C@H:17]2[O:18][C:19]([CH3:22])([CH3:21])[O:20][C@@H:16]2[C@H:15]([OH:23])[CH2:14][N:13]1[S:27]([C:30]1[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=1)(=[O:29])=[O:28])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 58866130HCID 58866130, compound

Product 1

HCID 58866159HCID 58866159, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above compound (2-2) (100 mg) was dissolved in methanol (2 mL) and 28% sodium methoxide (18 mg) was added, and then the mixture was stirred at room temperature for 2 hours. After neutralizing with a cation exchange resin, the insoluble material was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:2→1:1→2:1) to obtain the titled compound (69 mg).

Workup

  1. customthe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:2→1:1→2:1)

Sources & evidence

ORD record
ord-67465f1cc8b446189b0e162f837f03d1
Source dataset
uspto-grants-2007_05
Patent number
US07223779B2

Reaction notes

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