Sodium hydride → HCID 54546098, compound

HRID 2225658Notes

Reaction equation

HRID 2225658 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[H-].[Na+].S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH2:27][S:28]([C:31]1[CH:40]=[CH:39][C:34]([O:35][CH2:36][CH2:37]O)=[CH:33][CH:32]=1)(=[O:30])=[O:29]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:37][CH2:36][O:35][C:34]2[CH:33]=[CH:32][C:31]([S:28]([NH2:27])(=[O:30])=[O:29])=[CH:40][CH:39]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 85570p-ToluenesulfonateHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 19004336HCID 19004336, compound

Product 1

HCID 54546098HCID 54546098, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.905 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.218 g), stirred for 15 minutes and treated with the tosylate of 2-(4-aminosulfonylphenoxy)ethanol (1.67 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The material from ethyl acetate extraction was purified by HPLC (dichloromethane-ethyl acetate; 4:1) and crystallized from dichloromethane-hexane to provide 0.9 g of 4-[[2-[4-(amino-sulfonyl)phenoxy]ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester, mp 136°-137° C.

Workup

  1. extractionThe material from ethyl acetate extraction
  2. customwas purified by HPLC (dichloromethane-ethyl acetate; 4:1)
  3. customcrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-8a6224c1999344d58e93458706c43918
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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