HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,1'-Carbonyldiimidazole → N5-(4-hydroxy-3-sulfophenyl)-L-glutamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | (4S)-5-(tert-butoxy)-4-{[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acid | HCID 6993444 | — |
| Reactant | HCID 89373065 | HCID 89373065 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N5-(4-hydroxy-3-sulfophenyl)-L-glutamine | HCID 123936352 | — |
Reaction Steps
Boc-Glu-OtBu (100 mg, 0.33 mmol) was dissolved in methylene chloride (1 ml) and THF (1 ml), and CDI (65 mg, 1.1 mmol) was added to the solution. The mixture was stirred for 30 minutes at room temperature. Sodium 5-amino-2-hydroxybenzenesulfonate (77 mg, 0.33 mmol) was added to the mixture and stirred overnight at room temperature. After the solvent was removed by distillation, the mixture was purified in accordance with the purification step A. The resulting intermediate was dissolved in 2 ml of TFA. After stirring for 3 hours at room temperature, the solvent was distilled off. The mixture was purified according to 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-da5ed68168a3467994faa085e668d03a |
| Source note | uspto-grants-2015_04 |