Acetic Acid → HCID 56670358, compound

HRID 1469188Notes

Reaction equation

HRID 1469188 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]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[C:24]1[S:25][C:26]([Cl:40])=[C:27]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36]C(=O)C)=[CH:32][CH:31]=2)[CH:28]=1)(=O)C.C[O-].[Na+].CC(O)=O>CO>[Cl:40][C:26]1[S:25][C:24]([C@H:6]2[C@H:5]([OH:4])[C@@H:10]([OH:11])[C@H:9]([OH:15])[C@@H:8]([CH2:19][OH:20])[O:7]2)=[CH:28][C:27]=1[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 66693335HCID 66693335, compound

Product 1

HCID 56670358HCID 56670358, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of acetate 28 (413 mg, 0.617 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 29 (130 mg, 55%).

Workup

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

Sources & evidence

ORD record
ord-b88899af25fc449aa4953cdbde88e12d
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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