Potassium Hydroxide → HCID 12226278, compound

HRID 1415879Notes

Reaction equation

HRID 1415879 reaction equation
[OH-].[K+].C(N(CC)C(=O)[S:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[CH:10][C:9]=1[C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)C>CO.C1COCC1>[SH:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[CH:10][C:9]=1[C:18]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:25]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 88148662HCID 88148662, compound

Product 1

HCID 12226278HCID 12226278, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Potassium hydroxide pellets (58.6 g) was slowly added to a solution of the product (85.0 g) from step (j) dissolved in 1 L of methanol/THF (1:1). After refluxing for 3 hours, the reaction mixture was cooled to room temperature and concentrated in vacuo. The resulting residue was triturated with 1N HCl then extracted with EtOAc. The organic layer was separated, washed with 2×250 ml of 1N HCl then washed with 3×400 ml of 1N NaOH. The aqueous basic layers were combined and acidified with conc. HCl to afford the title product (54.8 g) as a gold solid. 1H NMR was consistent with the proposed structure.

Workup

  1. temperatureAfter refluxing for 3 hours
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was triturated with 1N HCl
  4. extractionthen extracted with EtOAc
  5. customThe organic layer was separated
  6. washwashed with 2×250 ml of 1N HCl
  7. washthen washed with 3×400 ml of 1N NaOH

Sources & evidence

ORD record
ord-0e49dd475cd04240b1d3d89709f33dfa
Source dataset
uspto-grants-1999_06
Patent number
US05910494

Reaction notes

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