Water → HCID 70391645, compound

HRID 637770Notes

Reaction equation

HRID 637770 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8](/[CH:25]=[CH:26]/[C:27]([CH3:33])([CH3:32])[CH2:28][CH2:29][CH2:30][CH3:31])[C@@H:9]1[C@@H:13]([CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH:12]([OH:23])[CH2:11][C@H:10]1[CH3:24].[C:34](=O)(O)[O-].[Na+].CI.O>CC(N(C)C)=O>[CH3:34][O:21][C:20](=[O:22])[CH2:19][CH2:18][CH2:17]/[CH:16]=[CH:15]\[CH2:14][C@@H:13]1[C@@H:9]([C@@H:8]([O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)/[CH:25]=[CH:26]/[C:27]([CH3:32])([CH3:33])[CH2:28][CH2:29][CH2:30][CH3:31])[C@H:10]([CH3:24])[CH2:11][CH:12]1[OH:23]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 70392372HCID 70392372, compound

Product 1

HCID 70391645HCID 70391645, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

The crude optically active (5Z,11alpha,13S,14E)-13-(2-tetrahydropyranyloxy)-11,16,16-trimethyl-9-hydroxyprosta-5,14-dien-1-oic acid (11.7 g) in dimethylacetamide (60 mL) solution was treated with sodium bicarbonate (14.0 g) and methyl iodide (13.0 mL). The mixture was stirred under argon at room temperature while protected from direct light for 25 hours. The mixture was then poured into water (200 mL) and the product was extracted three times using 100 mL hexane each time. The combined extracts were washed with water, aqueous methanol (1:1), and brine. After drying over sodium sulfate and evaporation of solvent, 11.1 g (92%) of crude optically active (5Z,11alpha,13S,14E)-13-(2-tetrahydro-pyranyloxy)-11,16,16-trimethyl-9-hydroxyprosta-5,14-dien-1-oic acid methyl ester was obtained as a yellow oil.

Workup

  1. extractionthe product was extracted three times
  2. washThe combined extracts were washed with water, aqueous methanol (1:1), and brine
  3. dry with materialAfter drying over sodium sulfate and evaporation of solvent, 11.1 g (92%) of crude optically active (5Z,11alpha,13S,14E)-13-(2-tetrahydro-pyranyloxy)-11,16,16-trimethyl-9-hydroxyprosta-5,14-dien-1-oic acid methyl ester
  4. customwas obtained as a yellow oil

Sources & evidence

ORD record
ord-c368cf4e100e4f6bb95d422b149d6c02
Source dataset
uspto-grants-1985_12
Patent number
US04558140

Reaction notes

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