HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (1R,2R)-N,1-dihydroxy-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | Hydroxyamine hydrochloride | HCID 443297 | — |
| Reactant | (1R,2R)-1-hydroxy-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylic acid | HCID 68818579 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Product | (1R,2R)-N,1-dihydroxy-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxamide | HCID 11856418 | 37% |
Reaction Steps
To a solution of (1R,2R)-1-hydroxy-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylic acid (0.08 g) in DMF (0.8 mL) was added hydroxylamine hydrochloride (2 eq), benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate (1.3 eq) and diisopropylethylamine (4 eq). The reaction was stirred overnight and injected directly onto a reverse phase HPLC (CH3CN/H2O) to afford (1R,2R)-N,1-dihydroxy-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxamide (0.03 g, 37%) as a white solid. MS: 472.1 (M+H)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07595327B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-2a66f603c8944f23ac6cecc8e850ba20 |
| Source note | uspto-grants-2009_09 |