Sodium Bicarbonate → HCID 86745148, compound

HRID 345233Notes

Reaction equation

HRID 345233 reaction equation
O1CCCCC1[O:7][C@H:8]1[C@H:22]([CH:23]=[CH:24][C@@H:25]([O:34]C2CCCCO2)[C@:26]([CH3:33])([O:31][CH3:32])[CH2:27][CH2:28][CH2:29][CH3:30])[C@@H:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:10](=[O:41])[CH2:9]1.C([O-])(O)=O.[Na+]>C(O)=O.O.C1COCC1>[OH:7][C@H:8]1[C@H:22]([CH:23]=[CH:24][C@@H:25]([OH:34])[C@:26]([CH3:33])([O:31][CH3:32])[CH2:27][CH2:28][CH2:29][CH3:30])[C@@H:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:10](=[O:41])[CH2:9]1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 131717029HCID 131717029, compound

Product 1

HCID 86745148HCID 86745148, compound

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the crude bis tetrahydropyranyl ether of Step C in formic acid, (16 ml), H2O (30 ml) and THF (35 ml) is stirred for 24 h at room temperature. The mixture is cooled in an ice-water bath, H2O (30 ml) is added, and solid NaHCO3 is added till a pH of 7 is reached. The aqueous layer is extracted with ether, the combined organic layers are washed with saturated NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo. Column chromatograph separation on silica gel, eluting with 2% MeOH in AcOEt, gives (8R,11R,12R,15R,16R)-11,15-dihydroxy-16-methyl-l6-methoxy-9-oxo-prost-13-en-1-oic acid, methyl ester which solidifies in the freezer (m.p. 44-45° C.).

Workup

  1. temperatureThe mixture is cooled in an ice-water bath
  2. extractionThe aqueous layer is extracted with ether
  3. washthe combined organic layers are washed with saturated NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customColumn chromatograph separation on silica gel
  7. washeluting with 2% MeOH in AcOEt

Sources & evidence

ORD record
ord-1b49621e7d3a4d6b8562821c15283fb8
Source dataset
uspto-grants-1991_10
Patent number
US05055592

Reaction notes

Loading…