Sodium Hydroxide → (5S,6R,7E,9E,11Z, 13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxa-7,9,11,13-hexadecatetraenoic acid

HRID 1354501Notes

Reaction equation

HRID 1354501 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([O:6][CH2:7][C@@H:8]([OH:28])/[CH:9]=[CH:10]/[CH:11]=[CH:12]\[CH:13]=[CH:14]\[CH:15]=[CH:16]\[C@@H:17]([OH:27])[C@@H:18]([OH:26])[CH2:19][O:20][CH2:21][C:22]([O:24]C)=[O:23])=[CH:4][CH:3]=1.[OH-].[Na+].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C@@H:8]([OH:28])/[CH:9]=[CH:10]/[CH:11]=[CH:12]\[CH:13]=[CH:14]\[CH:15]=[CH:16]\[C@@H:17]([OH:27])[C@@H:18]([OH:26])[CH2:19][O:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 62657Potassium Phosphate, TribasicHCID 10112981Acetic acid, (((2S,3R,4E,6E,8Z,10E,12S)-13-(4-fluorophenoxy)-2,3,12-trihydroxy-4,6,8,10-tridecatetraenyl)oxy)-, methyl ester

Product 1

HCID 10112100(5S,6R,7E,9E,11Z, 13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxa-7,9,11,13-hexadecatetraenoic acidYield 41,499.602%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  1. customPurification by chromatography on an HP20 column
  2. washeluted with an aqueous methanol gradient

Sources & evidence

ORD record
ord-70224b7cf8db429b98d5464a90bc277c
Source dataset
uspto-grants-2007_05
Patent number
US07223798B2

Reaction notes

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