4-Toluenesulfonyl chloride → Ethyl acetate hexane

HRID 273838Notes

Reaction equation

HRID 273838 reaction equation
[C:1]([O:5][C:6](N([C:13]1[C:22]2C(=CC=C[CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[C@H](CO)C)=[O:7])(C)(C)[CH3:2].S(Cl)([C:26]1C=CC(C)=CC=1)(=O)=O>N1C=CC=CC=1>[CH3:2][CH2:1][O:5][C:6]([CH3:26])=[O:7].[CH3:21][CH2:22][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 70093534N-t-butyloxycarbonylnaphthylalaninol

Product 1

HCID 21226206Ethyl acetate hexaneYield 214.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-30 °C

Procedure

N-t-butyloxycarbonylnaphthylalaninol (3.71 g; 12.3 mmol) was dissolved in pyridine (15 ml) and the solution was cooled to -30° C. Tosyl chloride (2.36 g; 12.4 mmol) was added and the mixture was stirred to clearness at -30° C. and then put into the refrigerator overnight. Pyridine was removed in vacuo and the product was extracted with ether (4×30 ml). The organic layer was washed with 1N HCl (2×30 ml), H2O (1×30 ml), NaHCO3 5% (2×30 ml) and saturated NaCl (1×30 ml), then dried over Na2SO4, filtered and stripped to leave an oily residue which was crystallized from AcOEt/hexane (4.6 g; 82% yield).

Workup

  1. customput into the refrigerator overnight
  2. customPyridine was removed in vacuo
  3. extractionthe product was extracted with ether (4×30 ml)
  4. washThe organic layer was washed with 1N HCl (2×30 ml), H2O (1×30 ml), NaHCO3 5% (2×30 ml) and saturated NaCl (1×30 ml)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customto leave an oily residue which

Sources & evidence

ORD record
ord-a8fbd839ba0b49efae388c8ec86f9e80
Source dataset
uspto-grants-1995_02
Patent number
US05387610

Reaction notes

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