Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | 3-Acetoxybenzoic acid | HCID 238669 | — |
| Reactant | HCID 57500365 | HCID 57500365 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57500364 | HCID 57500364 | 57.3% |
Reaction Steps
0.95 ml (6.80 mmol) of triethylamine and 1.50 g (3.40 mmol) of BOP are added, at ambient temperature, to 0.61 g (3.40 mmol) of 3-acetoxybenzoic acid in suspension in 20 ml of N,N-dimethylformamide. After 15 minutes, 1.0 g (3.09 mmol) of methyl 2-amino-5-[(1-amino-2-methylindolizin-3-yl)carbonyl]benzoate (described in Patent Application WO2003084956) in 10 ml of N,N-dimethylformamide is added. The reaction medium is stirred for 16 hours under argon and then diluted with ethyl acetate and washed with a saturated aqueous solution of sodium bicarbonate. The organic phase is washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. The solid obtained is taken up in acetone and then filtered and dried. 0.86 g (57%) of a greenish yellow powder is obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09120819B2 |
|---|
| Source dataset | uspto-grants-2015_09 |
|---|
| ORD ID | ord-48721f5922024a1da030af0e619f1eef |
|---|
| Source note | uspto-grants-2015_09 |
|---|