Acetic Acid → HCID 71077036, compound

HRID 576398Notes

Reaction equation

HRID 576398 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[CH:28]=[C:27]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([CH:36]4[CH2:38][CH2:37]4)=[CH:32][CH:31]=3)[C:26]([Cl:39])=[C:25]3[C:20]=2[CH2:21][CH2:22][CH2:23][O:24]3)[O:7][C@@H:6]1[CH2:40][O:41]C(=O)C)(=O)C.C[O-].[Na+].CC(O)=O>CO>[Cl:39][C:26]1[C:27]([CH2:29][C:30]2[CH:31]=[CH:32][C:33]([CH:36]3[CH2:38][CH2:37]3)=[CH:34][CH:35]=2)=[CH:28][C:19]([C@H:8]2[C@H:9]([OH:15])[C@@H:10]([OH:11])[C@H:5]([OH:4])[C@@H:6]([CH2:40][OH:41])[O:7]2)=[C:20]2[C:25]=1[O:24][CH2:23][CH2:22][CH2:21]2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 71110625HCID 71110625, compound

Product 1

HCID 71077036HCID 71077036, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of acetate 180 (152 mg, 0.24 mmol) in MeOH (5 mL) was added NaOMe (25 wt % in MeOH, 0.05 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 (reverse phase) to provide the compound E155 (37 mg, 34%).

Workup

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

Sources & evidence

ORD record
ord-4a6063a06f0e42b4b1933bd56bb2be92
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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