Sodium Hydroxide → Acetic acid, (((2S,3R,4E,6E,10E,12S)-13-(4-fluorophenoxy)-2,3,12-trihydroxy-4,6,10-tridecatrien-8-ynyl)oxy)-

HRID 2307611Notes

Reaction equation

HRID 2307611 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]/[C:11]#[C: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:30]=[CH:29][C:5]([O:6][CH2:7][C@@H:8]([OH:28])/[CH:9]=[CH:10]/[C:11]#[C: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:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 62657Potassium Phosphate, TribasicHCID 9823441Acetic acid, (((2S,3R,4E,6E,10E,12S)-13-(4-fluorophenoxy)-2,3,12-trihydroxy-4,6,10-tridecatrien-8-ynyl)oxy)-, methyl ester

Product 1

HCID 10111981Acetic acid, (((2S,3R,4E,6E,10E,12S)-13-(4-fluorophenoxy)-2,3,12-trihydroxy-4,6,10-tridecatrien-8-ynyl)oxy)-Yield 90.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (5S,6R,7E,9E,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxahexadeca-7,9,13-trien-11-ynoic acid, methyl ester, (0.4 g, 0.95 mmol) in methanol (20 mL) was treated with 1 N NaOH (aq) (4 mL, 4 mmol) solution and shaken and allowed to stand for three hours. The reaction mixture was then treated with saturated potassium monophosphate and poured onto an HP20 column. Elution with a gradient of methanol in water gave 0.35 g of (5S,6R,7E,9E,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxahexadeca-7,9,13-trien-11-ynoic acid, which solidified upon standing; 1H NMR (CD3OD) δ 3.63 (m, 2H), 3.667 (m, 1H), 3.91 (m, 2H), 4.113 (s, 2H), 4.150, (t, 1H), 4.498, (m, 1H), 5.762 (dd, 1H), 5.953 (dd, 1H), 6.003 (dt, 1H), 6.202(dd, 1H), 6.380 (dd, 1H), 6.596 (dd, 1H), 6.928 (m, 2H), 6.988 (m, 2H) ppm.

Workup

  1. additionpoured onto an HP20 column
  2. washElution with a gradient of methanol in water

Sources & evidence

ORD record
ord-b4afaefe55b94c378e6c450d2e840f52
Source dataset
uspto-grants-2004_12
Patent number
US06831186B2

Reaction notes

Loading…