Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | p-Toluenesulfonate | HCID 85570 | — |
| Reactant | Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester | HCID 3084696 | — |
| Reactant | HCID 19004336 | HCID 19004336 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 54546098 | HCID 54546098 | 47.2% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05344843 |
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| Source dataset | uspto-grants-1994_09 |
|---|
| ORD ID | ord-8a6224c1999344d58e93458706c43918 |
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| Source note | uspto-grants-1994_09 |
|---|
