Chloroform methanol → HCID 131719599, compound

HRID 864508Notes

Reaction equation

HRID 864508 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][C@H:9]3[C@@H:11]([O:22]COC)[C@H:12]([O:18]COC)[C@@H:13]([CH2:15][O:16][CH3:17])[O:14][C@H:8]3[N:7]([CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[C:6]=2[CH:33]=1.C(Cl)(Cl)Cl.CO>CO.Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][C@H:9]3[C@@H:11]([OH:22])[C@H:12]([OH:18])[C@@H:13]([CH2:15][O:16][CH3:17])[O:14][C@H:8]3[N:7]([CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[C:6]=2[CH:33]=1

Participants

5

Reactant 2

HCID 21584188Chloroform methanolHCID 86749914HCID 86749914, compound

Product 1

HCID 131719599HCID 131719599, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent2×

Procedure

The compound (26) 63 mg obtained in Example 25 was dissolved in 1 ml of methanol saturated with hydrogen chloride and 3 ml of methanol, and the solution was stirred for 2.5 hours at room temperature. The solution was concentrated under reduced pressure, the resulting residue was poured into 0.5N aqueous sodium hydroxide, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and saturated aqueous sodium chloride successively. The solution was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The resulting residue was purified by NH-silica gel column chromatography (manufactured by Fuji Silicia Company), and 47.2 mg (yield 78.5%) of the title compound was obtained from the fraction of chloroform-methanol (19:1).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionthe resulting residue was poured into 0.5N aqueous sodium hydroxide
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water, and saturated aqueous sodium chloride successively
  5. dry with materialThe solution was dried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe resulting residue was purified by NH-silica gel column chromatography (manufactured by Fuji Silicia Company)

Sources & evidence

ORD record
ord-b937b244ba1a4029a91e6b5c9c8cc666
Source dataset
uspto-grants-1996_10
Patent number
US05563137

Reaction notes

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