p-Toluenesulfonic acid monohydrate → p-Toluenesulfonic acid

HRID 637739Notes

Reaction equation

HRID 637739 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1>C(OCC)(=O)C>[C:2]1([CH3:12])[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 6101p-Toluenesulfonic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of p-toluenesulphonic acid monohydrate (1.34 g) and benzhydryl 6-(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopent-1-yl)penicillanate 1α-oxide (3.60 g) in ethyl acetate (25 ml) was stirred for 1.5 hours at room temperature. The solvent was evaporated under reduced pressure and the residue crystallised from diethyl ether to give yellow crystals of the p-toluenesulphonic acid salt of benzyhydryl 6-aminopenicillanate 1α-oxide (2.03 g). A solution of this tosylate in methylene chloride (25 ml) was washed twice with saturated aqueous sodium bicarbonate (25 ml) and then brine (25 ml), and then stirred rapidly for 3 hours at room temperature with phenoxyacetyl chloride (0.46 ml) and saturated aqueous sodium bicarbonate (25 ml). The organic layer was separated, washed with saturated aqueous sodium bicarbonate, dried with magnesium sulphate, and evaporated under reduced pressure to give the title compound as a foam, nmr (CDCl3) δ 1.03 (s, 3H), 1.60 (s, 3H), 4.46 (s, 1H), 4.64 (d, J=4 Hz, 1H), 5.42 (dd, J=4 and 8 Hz, 1H), 6.78 (d, J=4 Hz, 1H), 6.84 (s, 1H), 7.16 (s, 10H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue crystallised from diethyl ether

Sources & evidence

ORD record
ord-3dad02e5bd5b480e8404c100a29b5bce
Source dataset
uspto-grants-1985_12
Patent number
US04558124

Reaction notes

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