HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Hydroxide → (5S,6R,7E,9E,11Z, 13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxa-7,9,11,13-hexadecatetraenoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | Acetic acid, (((2S,3R,4E,6E,8Z,10E,12S)-13-(4-fluorophenoxy)-2,3,12-trihydroxy-4,6,8,10-tridecatetraenyl)oxy)-, methyl ester | HCID 10112981 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | (5S,6R,7E,9E,11Z, 13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxa-7,9,11,13-hexadecatetraenoic acid | HCID 10112100 | 41,499.602% |
Reaction Steps
A solution of (5S,6R,7E,9E,11Z,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxa-7,9,11,13-hexadecatetraenoic acid, methyl ester, (25 mg, 59 nMol) in methanol (6 mL) was treated with 1 N NaOH (aq) (25 μL, 25 μmol) solution and shaken and allowed to stand. Upon completion, the reaction was treated with saturated potassium monophosphate. Purification by chromatography on an HP20 column eluted with an aqueous methanol gradient gave 10 mg of (5S,6R,7E,9E,11Z, 13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxa-7,9,11,13-hexadecatetraenoic acid; 1H NMR (CD3OD) δ 3.6 (m, 3H), 3.88 (m, 4H), 4.18 (m, 1H), 4.52 (m, 1H), 5.84 (m, 2H), 6.03 (m, 2H), 6.34 (m, 2H), 6.74 (m, 1H), 6.95 (m, 5H) ppm.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06831186B2 |
| Source dataset | uspto-grants-2004_12 |
| ORD ID | ord-d2a2b38a8bd14777a2ad36fe6a5215ab |
| Source note | uspto-grants-2004_12 |