Acetic Acid → HCID 53325317, compound

HRID 2042933Notes

Reaction equation

HRID 2042933 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:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([CH2:27][C:28]3[S:29][C:30]([C:33]4[O:34][CH:35]=[CH:36][CH:37]=4)=[CH:31][N:32]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:38][O:39]C(=O)C)(=O)C.C[O-].[Na+].C(O)(=O)C>CO>[O:34]1[CH:35]=[CH:36][CH:37]=[C:33]1[C:30]1[S:29][C:28]([CH2:27][C:21]2[CH:20]=[C:19]([C@H:8]3[C@H:9]([OH:15])[C@@H:10]([OH:11])[C@H:5]([OH:4])[C@@H:6]([CH2:38][OH:39])[O:7]3)[CH:24]=[CH:23][C:22]=2[C:25]#[N:26])=[N:32][CH:31]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 67995547HCID 67995547, compound

Product 1

HCID 53325317HCID 53325317, compoundYield 20,285.699%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the peracetylate 59 (208 mg, 0.35 mmol) in MeOH (10 mL) was added NaOMe (25 wt. % in MeOH, 0.2 mL). The reaction mixture was stirred at ambient temperature for 3 h. Acetic acid was added to neutralize the reaction mixture and concentrated in vacuo. The residue was redissolved in MeOH and further purified by prep HPLC (C18) to provide the titled compound (106 mg, 71 mmol) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was redissolved in MeOH
  3. customfurther purified by prep HPLC (C18)

Sources & evidence

ORD record
ord-0ee9f060ce5249cdbe9959d37da22906
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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