4-Toluenesulfonyl chloride → Ethyl acetate hexane

HRID 52201Notes

Reaction equation

HRID 52201 reaction equation
N([C:28]([O:30][C:31]([CH3:34])(C)C)=[O:29])[C@H:2]([C:14]([CH2:16]OS(C1C=CC(C)=CC=1)(=O)=O)=O)[CH2:3][C:4]1C=C2C(C=CC=C2)=C[CH:5]=1.[C:35](OC(N(C1C2C(=CC=CC=2)C=CC=1)[C@H](CO)C)=O)(C)(C)C.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>N1C=CC=CC=1>[CH3:34][CH2:31][O:30][C:28]([CH3:35])=[O:29].[CH3:16][CH2:14][CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 70093534N-t-butyloxycarbonylnaphthylalaninolHCID 131719947HCID 131719947, compound

Product 1

HCID 21226206Ethyl acetate hexaneYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-30 °C

Procedure

Boc-Nal-CH2OTs. 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-fdeb293275524430832ed2aac56fc5ac
Source dataset
uspto-grants-1997_04
Patent number
US05616605

Reaction notes

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