Sulfuric Acid → HCID 67809210, compound

HRID 275608Notes

Reaction equation

HRID 275608 reaction equation
[OH:1][CH2:2][C:3]([S:6]([CH2:9][CH:10]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])(=[O:8])=[O:7])([CH3:5])[CH3:4].[CH3:28][O:29][CH2:30][C:31](Cl)=[O:32].S(=O)(=O)(O)O>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH3:28][O:29][CH2:30][C:31]([O:1][CH2:2][C:3]([S:6]([CH2:9][CH:10]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])(=[O:8])=[O:7])([CH3:5])[CH3:4])=[O:32]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 96623Methoxyacetyl chlorideHCID 54448487HCID 54448487, compound

Product 1

HCID 67809210HCID 67809210, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 422 mg (1.08 mmol) of benzyl rac-α-[[(2-hydroxyl-1,1-dimethylethyl)sulfonyl]methyl]hydrocinnamate, 2 ml (2.2 mmol) of methoxyacetyl chloride and 100 mg (0.8 mmol) of 4-dimethylaminopyridine in 2 ml of pyridine was stirred at 900 for 15 hours. Subsequently, the mixture was poured on to ice and 150 ml of 3N sulphuric acid and extracted three times with 300 ml of ether each time. The organic extracts were then washed with in each case 150 ml of ice-cold 3N sulphuric acid, water, 1M sodium hydrogen carbonate solution and saturated sodium chloride solution, then dried over magnesium sulphate and evaporated under reduced pressure. For purification, the crude product (540 mg of brown oil) was chromatographed on 50 g of silica gel with a 4:1 mixture of toluene and ethyl acetate. There were obtained 180 mg of benzyl rac-α-[[[2-(methoxyacetoxy)-1,1-dimethylethyl]sulfonyl]methyl]hydrocinnamate as a colourless oil, MS: 463 (M+H)+.

Workup

  1. extractionextracted three times with 300 ml of ether each time
  2. washThe organic extracts were then washed with in each case 150 ml of ice-cold 3N sulphuric acid, water, 1M sodium hydrogen carbonate solution and saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customFor purification
  6. customthe crude product (540 mg of brown oil) was chromatographed on 50 g of silica gel with a 4:1 mixture of toluene and ethyl acetate

Sources & evidence

ORD record
ord-6aa256cfea794f57a8560b2a1959b651
Source dataset
uspto-grants-1995_02
Patent number
US05393875

Reaction notes

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