HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 3-{[({(1R,2S)-2-[(tert-butoxycarbonyl)amino]cyclopentyl}carbonyl)amino]sulfonyl}propylacetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | (1R,2S)-2-(tert-Butoxycarbonylamino)cyclopentanecarboxylic acid | HCID 1268160 | — |
| Reactant | 5-Sulfamoylpentanoic acid | HCID 57172024 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-{[({(1R,2S)-2-[(tert-butoxycarbonyl)amino]cyclopentyl}carbonyl)amino]sulfonyl}propylacetic acid | HCID 67429160 | — |
Reaction Steps
A mixture of (1R,2S)-2-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylic acid (1.0 g), DMF (10 ml), 3-(aminosulfonyl)propylacetic acid (0.95 ml), CDI(0.85 g), and DBU (0.80 g) was stirred at room temperature for 3 days. To the reaction mixture were added 1 M hydrochloric acid and ethyl acetate, and the organic layer was separated. The organic layer was washed with a saturated sodium bicarbonate solution, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 3-{[({(1R,2S)-2-[(tert-butoxycarbonyl)amino]cyclopentyl}carbonyl)amino]sulfonyl}propylacetic acid (1.2 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08030489B2 |
| Source dataset | uspto-grants-2011_10 |
| ORD ID | ord-bb5c414b732946879f0544db0e3c03ae |
| Source note | uspto-grants-2011_10 |