Dimethyl Sulfoxide → HCID 70391994, compound

HRID 1607742Notes

Reaction equation

HRID 1607742 reaction equation
CS(C)=O.[CH3:5][O:6][C:7](=[O:38])[CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][C@@H:14]1[C@@H:18]([C@@H:19]([O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)/[CH:20]=[CH:21]/[C:22]([CH3:28])([CH3:27])[CH2:23][CH2:24][CH2:25][CH3:26])[C@H:17]([CH3:36])[CH2:16][CH:15]1[OH:37].C(N(CC)CC)C>[Cl-].[Na+].O>[CH3:5][O:6][C:7](=[O:38])[CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][C@@H:14]1[C@@H:18]([C@@H:19]([O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)/[CH:20]=[CH:21]/[C:22]([CH3:27])([CH3:28])[CH2:23][CH2:24][CH2:25][CH3:26])[C@H:17]([CH3:36])[CH2:16][C:15]1=[O:37]

Participants

5

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 8471TriethylamineHCID 70391645HCID 70391645, compound

Product 1

HCID 70391994HCID 70391994, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A DMSO (60 mL) solution of the crude optically active (5Z,11alpha,13S,14E)-13-(2-tetrahydropyranyloxy)-11,16,16-trimethyl-9-hydroxyprosta-5,14-dien-1-oic acid methyl ester (11.1 g) was treated with triethylamine (22 mL) and then dropwise with a DMSO (60 mL) solution of sulfur trioxide pyridine complex (11.1 g) during 30 minutes while stirring. After 31/2 hours, the reaction mixture was poured into a slush of ice and brine (600 mL) and extracted with hexane (3×150 mL). The combined extracts were washed with 2 N HCL, water, NaHCO3 solution, and brine, then dried over sodium sulfate and stripped of solvent. The crude optically active (5Z,11alpha,13S,14E)-13-(2-tetrahydropyranyloxy)-11,16,16-Trimethyl-9-oxoprosta-5,14-dien-1-oic acid methyl ester was obtained as a yellow oil weighing 10.55 g (95.4%).

Workup

  1. extractionextracted with hexane (3×150 mL)
  2. washThe combined extracts were washed with 2 N HCL, water, NaHCO3 solution, and brine
  3. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-3be10ca013a24221b57736239fc8fa17
Source dataset
uspto-grants-1989_09
Patent number
US04866205

Reaction notes

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