Potassium Hydroxide → HCID 178515829, compound

HRID 1953633Notes

Reaction equation

HRID 1953633 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH:12]3[NH:14][CH:9]2[CH2:10][CH2:11]3)=[CH:4][N:3]=1.[OH-:15].[K+]>C(O)(C)(C)C>[OH:15][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH:12]3[NH:14][CH:9]2[CH2:10][CH2:11]3)=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22468072HCID 22468072, compound

Product 1

HCID 178515829HCID 178515829, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Compound 53 (8.5 mg, 0.044 mmol) was dissolved in 1 ml tert-butanol. To this solution was added 1 ml 2M potassium hydroxide. After reflux for 20 hours and evaporation of butanol, the mixture was adjusted with 1M hydrochloric acid to pH 6-7. Evaporation of solvent in vacuo and purification of product with silica gel preparative thin layer chromatography developing with 20% 7N ammonia methanol in chloroform gave 4.2 mg compound 77 as an oil. Yield 50%. MS(CI) 191(M+1). 1H-NMR (CDCl3) δ 2.554 (br.s., 1H, H2), 3.503; 3.743 (2br.s., 2H, H1,4).

Workup

  1. temperatureAfter reflux for 20 hours
  2. customevaporation of butanol
  3. customEvaporation of solvent
  4. customin vacuo and purification of product with silica gel preparative thin layer chromatography

Sources & evidence

ORD record
ord-3e8392b66a524df88eb7b7b36cf5b256
Source dataset
uspto-grants-2000_09
Patent number
US06117889

Reaction notes

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