HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium 2-ethylhexanoate → (2R,3R,4S,5R,6E)-7-cyclopentyl-3,4,5-trihydroxy-2-methoxy-N-[(3S)-4-oxo-9-phenyl-2,3,4,5-tetrahydro-1,5-benzoxazepin-3-yl]hept-6-enamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium 2-ethylhexanoate | HCID 23672331 | — |
| Reactant | (3R,4R,5S)-5-[(1R,2E)-3-cyclopentyl-1-hydroxyprop-2-en-1-yl]-4-hydroxy-3-methoxydihydrofuran-2(3H)-one | HCID 57463784 | — |
| Reactant | (3S)-3-amino-9-phenyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one hydrochloride | HCID 67328839 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (2R,3R,4S,5R,6E)-7-cyclopentyl-3,4,5-trihydroxy-2-methoxy-N-[(3S)-4-oxo-9-phenyl-2,3,4,5-tetrahydro-1,5-benzoxazepin-3-yl]hept-6-enamide | HCID 57617789 | — |
Reaction Steps
100 mg of 32 (390 μmol), 113 mg of 38 (390 μmol) and 162 mg of sodium 2-ethylhexanoate (0.98 mmol) in 2 mL of THF are successively introduced into a Wheaton tube, with stirring and under an argon atmosphere. The stirring is maintained at RT for 24 h. The reaction medium is concentrated to dryness. The residues are chromatographed on a silica cartridge (8 g, eluent AcOEt). 79 mg of expected product Ex16 are recovered.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07994161B2 |
| Source dataset | uspto-grants-2011_08 |
| ORD ID | ord-3779798dbc3e4e50b373d78f00a6c3d9 |
| Source note | uspto-grants-2011_08 |