Sodium Bicarbonate → 17-phenyl-trinor-PGF2alpha isopropyl ester

HRID 599529Notes

Reaction equation

HRID 599529 reaction equation
[Si]([O:8][C@@H:9]([CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)/[CH:10]=[CH:11]/[C@H:12]1[C@H:16]([O:17][Si](C(C)(C)C)(C)C)[CH2:15][C@H:14]([OH:25])[C@@H:13]1[CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33])(C(C)(C)C)(C)C.C([O-])(O)=O.[Na+]>CC(O)C>[OH:17][C@@H:16]1[CH2:15][C@H:14]([OH:25])[C@H:13]([CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33])[C@H:12]1/[CH:11]=[CH:10]/[C@@H:9]([OH:8])[CH2:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67226382HCID 67226382, compound

Product 1

HCID 528310717-phenyl-trinor-PGF2alpha isopropyl esterYield 111%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of compound (11b) (60 g) prepared in EXAMPLE 20 and aqueous HF (2N, 135 mL) in IPA (240 mL) was stirred. Saturated aqueous NaHCO3 (120 mL) was added and the mixture was extracted with EtOAc (600 mL). The separated aqueous layer was extracted with EtOAc (300 mL) and the combined organic layer was washed with saturated aqueous NaCl (300 mL), dried with Na2SO4, filtered, and the filter cake was washed with EtOAc (200 mL). The filtrate was concentrated to furnish 43.5 g of crude compound (11c) (84.3% HPLC purity, 84% yield) which was directly used without purification in EXAMPLE 22.

Workup

  1. extractionthe mixture was extracted with EtOAc (600 mL)
  2. extractionThe separated aqueous layer was extracted with EtOAc (300 mL)
  3. washthe combined organic layer was washed with saturated aqueous NaCl (300 mL)
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. washthe filter cake was washed with EtOAc (200 mL)
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0db77b0572314e3c8a3fddfbfbcff4ea
Source dataset
uspto-grants-2011_03
Patent number
US07897795B2

Reaction notes

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