p-Toluenesulfonic acid → HCID 10834640, compound

HRID 419760Notes

Reaction equation

HRID 419760 reaction equation
[OH:1][C@@H:2]([C@@H:18]1[CH2:22][O:21]C(C)(C)[N:19]1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CO>[OH:21][CH2:22][C@H:18]([NH:19][C:25](=[O:26])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C@H:2]([OH:1])[C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acid2×HCID 516892Sodium BicarbonateHCID 10694286HCID 10694286, compound

Product 1

HCID 10834640HCID 10834640, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The (S)-tert-butyl 4-((R)-1-hydroxy-2-hexadecynyl)-2,2-dimethyloxazolidine-3-carboxylate) (100 mg, 0.23 mmol) obtained in the above-described reaction was dissolved in methanol (4.4 ml); p-toluenesulfonic acid (0.8 mg, 4.6 μmol) was added to the solution, and the mixture was stirred at room temperature for 12 hours. P-toluenesulfonic acid (0.8 mg, 4.6 μmol) was added to this reaction mixture, stirred for 6 hours, heated to 60° C., and further stirred for 2 hours. Saturated sodium hydrogen carbonate was added to this reaction mixture, and the reaction was stopped; the mixture was subsequently extracted with ethyl acetate, and the organic layer was dried and filtered. The resulting filtrate was purified by column chromatography to produce tert-butyl (2S,3R)-1,3-dihydroxyoctadec-4-yn-2-ylcarbamate (85 mg, 93% yield).

Workup

  1. stirringstirred for 6 hours
  2. temperatureheated to 60° C.
  3. stirringfurther stirred for 2 hours
  4. extractionthe mixture was subsequently extracted with ethyl acetate
  5. customthe organic layer was dried
  6. filtrationfiltered
  7. customThe resulting filtrate was purified by column chromatography

Sources & evidence

ORD record
ord-c626e4c342b9434fa7f1e48f32104d25
Source dataset
uspto-grants-2012_01
Patent number
US08093395B2

Reaction notes

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