Sodium Methoxide → HCID 70650761, compound

HRID 2042939Notes

Reaction equation

HRID 2042939 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]([N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]([CH2:28][C:29]3[S:30][C:31]([C:34]4[O:35][CH:36]=[CH:37][CH:38]=4)=[CH:32][N:33]=3)=[CH:20]2)[O:7][C@@H:6]1[CH2:39][O:40]C(=O)C)(=O)C.C[O-].[Na+]>CO>[O:35]1[CH:36]=[CH:37][CH:38]=[C:34]1[C:31]1[S:30][C:29]([CH2:28][C:21]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:19]([C@H:8]3[C@H:9]([OH:15])[C@@H:10]([OH:11])[C@H:5]([OH:4])[C@@H:6]([CH2:39][OH:40])[O:7]3)[CH:20]=2)=[N:33][CH:32]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 70651006HCID 70651006, compound

Product 1

HCID 70650761HCID 70650761, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of acetate 79 (195 mg, 0.32 mmol) in MeOH (15 mL) were added sodium methoxide (25 wt. % in MeOH, 1 mL) at room temperature. The mixture was stirred at room temperature for 1 hours. The amberlite IR-120H resin was added to the mixture to acidify the mixture. The mixture was filtered off and the filtrate was concentrated in vacuo. The residue was purified by prep HPLC (C18) to provide the titled compound 80 (25 mg, 18%).

Workup

  1. additionThe amberlite IR-120H resin was added to the mixture
  2. filtrationThe mixture was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by prep HPLC (C18)

Sources & evidence

ORD record
ord-b9d97283f03844bca3d699a0f6142936
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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