Sodium Hydroxide → HCID 178482827, compound

HRID 2351015Notes

Reaction equation

HRID 2351015 reaction equation
[OH:1][CH:2]([C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=1)[CH2:3][NH:4][C:5]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[N:6][CH2:7][CH2:8][S:9][CH2:10][C:11]1[O:12][C:13]([CH2:16][N:17](C)[C:18](OCC(Cl)(Cl)Cl)=O)=[CH:14][CH:15]=1.P([O-])(O)(O)=O.[K+].[OH-].[Na+]>O1CCCC1.[Zn]>[OH:1][CH:2]([C:32]1[CH:33]=[CH:34][C:35]([OH:38])=[CH:36][CH:37]=1)[CH2:3][NH:4][C:5]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[N:6][CH2:7][CH2:8][S:9][CH2:10][C:11]1[O:12][C:13]([CH2:16][NH:17][CH3:18])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 516951Monobasic potassium phosphateHCID 178482829HCID 178482829, compound

Product 1

HCID 178482827HCID 178482827, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In 370 ml of tetrahydrofuran was dissolved 26.9 g of N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-N'-methanesulfonyl-N"-[2-[[5-[N-methyl-N-(2,2,2trichloroethoxycarbonyl)aminomethyl]-2-furyl]methylthio] -ethyl]guanidine. Thereto were added 320 ml of a 0.5 M aqueous potassium dihydrogen phosphate solution and 42 g of an active zinc powder, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was adjusted to pH 9.8 with a 5N aqueous sodium hydroxide solution and extracted with 370 ml of ethyl acetate. The solvent of the extract was removed by distillation under reduced pressure. The residue thus obtained was purified by a column chromatography (eluant:chloroform:methanol:aqueous ammonia solution=85:15:1) and then recrystallized from 95% aqueous ethanol solution to obtain 12.6 g (yield: 65%) of N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-N'-methanesulfonyl-N"-[2-[[5-(methylamino)methyl-2-furyl]methylthio]ethyl]guanidine having a melting point of 146.5° to 147° C..

Workup

  1. extractionextracted with 370 ml of ethyl acetate
  2. customThe solvent of the extract was removed by distillation under reduced pressure
  3. customThe residue thus obtained
  4. customwas purified by a column chromatography (eluant:chloroform:methanol:aqueous ammonia solution=85:15:1)
  5. customrecrystallized from 95% aqueous ethanol solution

Sources & evidence

ORD record
ord-c2cae5c8291b4eb3b12ce6c696179535
Source dataset
uspto-grants-1989_10
Patent number
US04871765

Reaction notes

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