Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | HCID 86761650 | HCID 86761650 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 68485386 | HCID 68485386 | 79.2% |
Reaction Steps
Lithium hydroxide (0.068 g, 2.85 mmol) was added to a solution of 1-(1,1-dimethylethyl)2-ethyl 6-[(methylsulfonyl)amino]-1H-indole-1,2-dicarboxylate (0.109 g, 0.285 mmol) in THF:methanol:water/3:1:1 (3 mL). The mixture was heated at 50° C. for 2 hrs. The solvent was evaporated and the residue was dissolved in water, acidified with 1N aqueous HCl and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated to give the title compound (0.040 g, 55%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.92 (br. s., 1H), 11.41-11.79 (m, 1H), 9.32-9.73 (m, 1H), 7.48-7.57 (m, 1H), 7.31 (s, 1H), 6.94-7.00 (m, 1H), 6.88-6.94 (m, 1H), 2.88 (s, 3H). ES MS: m/z 253 (M−1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08304419B2 |
|---|
| Source dataset | uspto-grants-2012_11 |
|---|
| ORD ID | ord-0a79a36f301845d5848254ccf8f47133 |
|---|
| Source note | uspto-grants-2012_11 |
|---|