HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Aminobenzenesulfonic acid → N5-(3-sulfophenyl)-L-glutamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Aminobenzenesulfonic acid | HCID 8474 | — |
| Reactant | HOAt | HCID 181649 | — |
| Reactant | (4S)-5-(tert-butoxy)-4-{[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acid | HCID 6993444 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | N5-(3-sulfophenyl)-L-glutamine | HCID 45275583 | 41% |
Reaction Steps
Boc-Glu-OtBu (75 mg, 0.247 mmol), HATU (112 mg, 0.296 mmol) and HOAt (41 mg, 0.296 mmol) were dissolved in 1 ml of DMF, and triethylamine (52 μl) was added to the solution. The mixture was stirred at room temperature for 10 minutes. 3-Sulfoaniline (43 mg, 0.247 mmol) was added to the mixture, followed by stirring at room temperature overnight. After the solvent was removed by distillation, the mixture was purified according to the purification step A. The resulting intermediate was dissolved in 2 ml of trifluoroacetic acid. After stirring for 3 hours at room temperature, the solvent was distilled off. The product was purified using the purification step A to give the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09000208B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-ea73242ef9844bcba8bcc3dd787843ff |
| Source note | uspto-grants-2015_04 |