Sodium hydride → HCID 19787978, compound

HRID 1656376Notes

Reaction equation

HRID 1656376 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[N:18](S(C1C=CC(C)=CC=1)(=O)=O)[C:17]1[CH:16]=[N:15][C:14]([CH:32]([OH:39])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[C:13]([CH2:40][O:41][CH3:42])[C:12]2=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].[H-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[CH:16]=[N:15][C:14]([CH:32]([OH:39])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[C:13]([CH2:40][O:41][CH3:42])[C:12]2=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10942334Sodium MethoxideHCID 19787965HCID 19787965, compound

Product 1

HCID 19787978HCID 19787978, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

300 mg of 6-benzyloxy-3-(1-hydroxy-1-phenylmethyl)4methoxymethyl-9-(4-methylphenylsulfonyl)-beta-carboline was added a sodium methylate solution of 50 mg of 80% sodium hydride and 30 ml of absolute ethanol and refluxed for 2 hours under argon. After distilling off the solvent, the residue was taken up in ethyl acetate and washed with saturated sodium chloride solution. After column chromatography on silica gel in the system of dichloromethane/ethanol 12:1, 211 mg of the title compound was obtained after recrystallization from ethyl acetate/petroleum ether from the ethyl acetate phase dried on magnesium sulfate and concentrated by evaporation, melting point 190°-191° C.

Workup

  1. temperaturerefluxed for 2 hours under argon
  2. distillationAfter distilling off the solvent
  3. washwashed with saturated sodium chloride solution

Sources & evidence

ORD record
ord-ea3718bfba934515950e34cb4c0926b8
Source dataset
uspto-grants-1993_10
Patent number
US05254563

Reaction notes

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