HuagongsheHuagongshe Chemistry Print Report · For research reference only
(S)-7-Amino-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one hydrochloride → (2R,3R,4S,5R,6E)-7-cyclopentyl-2-ethoxy-3,4,5-trihydroxy-N-[(3S)-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepin-3-yl]hept-6-enamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (S)-7-Amino-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one hydrochloride | HCID 18599716 | — |
| Reactant | Sodium 2-ethylhexanoate | HCID 23672331 | — |
| Reactant | (3R,4R,5S)-5-[(1R,2E)-3-cyclopentyl-1-hydroxyprop-2-en-1-yl]-3-ethoxy-4-hydroxydihydrofuran-2(3H)-one | HCID 67329167 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (2R,3R,4S,5R,6E)-7-cyclopentyl-2-ethoxy-3,4,5-trihydroxy-N-[(3S)-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepin-3-yl]hept-6-enamide | HCID 57617795 | — |
Reaction Steps
110 mg of 52 (407 μmol), 87 mg of 4 (407 μmol) and 169 mg of sodium 2-ethylhexanoate (1.02 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). 75 mg of expected product Ex20 are recovered.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07994161B2 |
| Source dataset | uspto-grants-2011_08 |
| ORD ID | ord-3e4d5b02dbdc4f44942f20ee032d85f0 |
| Source note | uspto-grants-2011_08 |