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)-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-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 | (S)-3-Amino-1-methyl-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one hydrochloride | HCID 67345769 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (2R,3R,4S,5R,6E)-7-cyclopentyl-3,4,5-trihydroxy-2-methoxy-N-[(3S)-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]hept-6-enamide | HCID 57463782 | — |
Reaction Steps
100 mg of 19 (0.39 mmol), 88.42 mg of 8a (0.39 mmol) and 162 mg of sodium 2-ethylhexanoate (0.98 mmol) in 2.0 ml of THF are successively introduced into a Wheaton tube, with agitation and under an argon atmosphere. The agitation is maintained at AT for 24 h. The reaction medium is directly evaporated to dryness. The crude is chromatographed on a silica cartridge (12 g, eluent EtOAc), and 60 mg of expected product Ex6 (white solid) are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07994162B2 |
| Source dataset | uspto-grants-2011_08 |
| ORD ID | ord-8ce37e0103a543188413b0ced4165e58 |
| Source note | uspto-grants-2011_08 |