Acetic Acid → HCID 56670267, compound

HRID 1469197Notes

Reaction equation

HRID 1469197 reaction equation
C([O:4][C@H:5]1[C@H:10]([O:11]C(=O)C)[C@@H:9]([O:15]C(=O)C)[C@H:8]([C:19]2[S:20][C:21]([Cl:32])=[C:22]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)[CH:23]=2)[O:7][C@@H:6]1[CH2:33][O:34]C(=O)C)(=O)C.C[O-].[Na+].CC(O)=O>CO>[Cl:32][C:21]1[S:20][C:19]([C@H:8]2[C@H:9]([OH:15])[C@@H:10]([OH:11])[C@H:5]([OH:4])[C@@H:6]([CH2:33][OH:34])[O:7]2)=[CH:23][C:22]=1[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 66691711HCID 66691711, compound

Product 1

HCID 56670267HCID 56670267, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of acetate 40 (339 mg, 0.612 mmol) in MeOH (15 mL) was added NaOMe (25 wt % in MeOH, 0.2 mL) at room temperature. The mixture was stirred at room temperature for 1 hour. Glacial AcOH was added to the mixture to acidify the mixture. The mixture was concentrated under reduced pressure. The residue was purified by prep HPLC (C18) to provide the title compound 41 (55 mg, 23%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe residue was purified by prep HPLC (C18)

Sources & evidence

ORD record
ord-be40dd6098c3423f8c54295ec1ea3a98
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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