HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → (Z)-7-{(1R,2S,3R)-3-Hydroxy-2-[1-(4-methoxy-benzyloxy)-indan-5-yl]-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (Z)-7-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[1-(4-methoxy-benzyloxy)-indan-5-yl]-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester | HCID 69367144 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Product | (Z)-7-{(1R,2S,3R)-3-Hydroxy-2-[1-(4-methoxy-benzyloxy)-indan-5-yl]-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester | HCID 69595718 | 69.8% |
Reaction Steps
A mixture of 15-4 (20 mg, 0.032 mmol) in acetic acid (0.3 mL)/water (0.1 mL)/THF (0.1 mL) was stirred at room temperature. After two days, saturated NaHCO3 solution was added and the resulting mixture was extracted with dichloromethane (3×20 mL). The combined dichloromethane solution was dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel (20% ethyl acetate/hexanes→30% →40%) which gave the title compound (11 mg, 67%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07091231B2 |
| Source dataset | uspto-grants-2006_08 |
| ORD ID | ord-37fac7bdf06c46dc8609a5f9d997917f |
| Source note | uspto-grants-2006_08 |