HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Hydroxide → 1-Methyl-1H-imidazole-4-sulfonic acid {2-[8-(3,4-dichloro-benzyl)-7-formylamino-5,6,7,8-tetrahydro-naphthalen-2-yloxy]-ethyl}-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | Ethyl 1-(3,4-dichlorobenzyl)-7-(2-(1-methyl-1H-imidazole-4-sulfonamido)ethoxy)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate | HCID 46870449 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1-Methyl-1H-imidazole-4-sulfonic acid {2-[8-(3,4-dichloro-benzyl)-7-formylamino-5,6,7,8-tetrahydro-naphthalen-2-yloxy]-ethyl}-amide | HCID 57487077 | 65% |
Reaction Steps
Ethyl 1-(3,4-dichlorobenzyl)-7-(2-(1-methyl-1H-imidazole-4-sulfonamido)ethoxy)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (example 3, 60.0 mg, 0.103 mmol) was dissolved in THF (5 ml) and LiAlH4 (7.83 mg, 0.206 mmol) was added at RT. The residue was added to 2N NaOH and extracted with dichloromethane. The organic layer was washed with saturated NaHCO3 solution and then with saturated NaCl solution, dried and evaporated. The product was precipitated as an HCl salt from 6N HCl in isopropanol and isopropylether to obtain the product as a white salt (36 mg, 61%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09096619B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-6a03092729a4459bac1e0531642132f1 |
| Source note | uspto-grants-2015_08 |