Acetic Acid → HCID 56677129, compound

HRID 1469184Notes

Reaction equation

HRID 1469184 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:33])=[C:22]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[CH:23]=2)[O:7][C@@H:6]1[CH2:34][O:35]C(=O)C)(=O)C.C[O-].[Na+].CC(O)=O>CO>[Cl:33][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]([CH2:34][OH:35])[O:7]2)=[CH:23][C:22]=1[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 66691926HCID 66691926, compound

Product 1

HCID 56677129HCID 56677129, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of acetate 19 (1.37 g, 2.41 mmol) in MeOH (20 mL) was added NaOMe (25 wt % in MeOH, 0.3 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 20 (604 mg, 63%).

Workup

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

Sources & evidence

ORD record
ord-fb6533a9a7914fd981b6e35b754ec988
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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