Potassium Hydroxide → HCID 178515829, compound

HRID 399088Notes

Reaction equation

HRID 399088 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-45e24131d76a4ed198ff378a30fe6076
Source dataset
uspto-grants-1998_10
Patent number
US05817679

Reaction notes

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