Sodium Methoxide → HCID 53318599, compound

HRID 2042944Notes

Reaction equation

HRID 2042944 reaction equation
CC1C=CC(S([O:11][CH2:12][C@@H:13]2[C@@H:18]([OH:19])[C@H:17]([OH:20])[C@@H:16]([OH:21])[C@H:15]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([CH2:29][C:30]4[S:31][C:32]([C:35]5[O:36][CH:37]=[CH:38][CH:39]=5)=[CH:33][N:34]=4)[CH:23]=3)[O:14]2)(=O)=O)=CC=1.[CH3:40][O-].[Na+]>CO>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([C@H:15]2[C@H:16]([OH:21])[C@@H:17]([OH:20])[C@H:18]([OH:19])[C@@H:13]([CH2:12][O:11][CH3:40])[O:14]2)=[CH:23][C:24]=1[CH2:29][C:30]1[S:31][C:32]([C:35]2[O:36][CH:37]=[CH:38][CH:39]=2)=[CH:33][N:34]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86680891HCID 86680891, compound

Product 1

HCID 53318599HCID 53318599, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solution of toluenesulfonate 90 (104 mg, 0.18 mmol) and NaOMe (25 wt. % in MeOH, 5 mL) in methanol (3.5 mL) was stirred at room temperature for 15 h. After reaction complete, the resulting solution was quenched with H2O. Reaction mixture was evaporated under reduced pressure. The residue was purified by prep HPLC (C18) to afford the titled compound 91 (12 mg, 56%) as a solid.

Workup

  1. customAfter reaction complete
  2. customthe resulting solution was quenched with H2O
  3. customReaction mixture
  4. customwas evaporated under reduced pressure
  5. customThe residue was purified by prep HPLC (C18)

Sources & evidence

ORD record
ord-bd274fd9ed6b4af4946e0f27a529b801
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

Loading…