Hexane → p-Toluenesulfonic acid

HRID 543119Notes

Reaction equation

HRID 543119 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.CCCCCC>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

4

Reactant 2

HCID 8058HexaneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 6101p-Toluenesulfonic acidYield 320.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Diphenylmethyl-3-[(1-methyl-1H-tetrazol-5-yl) thiomethyl]-7α-methylthio-7β-(4-nitrobenzylideneamino)-1-oxadethia-ceph-3-em-4-carboxylate (471 mg; 0.72 mmol) was dissolved in ethyl acetate (2 ml) and a solution of toluene-p-sulphonic acid monohydrate (149 mg; 0.78 mmol) in a little ethyl acetate added. After stirring at room temperature for 1 hour, hexane was added to complete the precipitation of the product, which was filtered off, washed well with ethyl acetate, ether and dried in vacuo to give diphenylmethyl 7-β-amino-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]-7α-methylthio-1-oxadethia-ceph-3-em-4-carboxylate, p-toluene sulphonic acid salt (431 mg; 93%). νmax (Nujol) 3400, 1795, 1720, 1620 cm-1 ; δppm [(CD3)2SO] 2.28 (3H,s), 2.41 (3H,s), 3.4-3.6(3H, broad s), 3.89 (3H,s), 4.28(2H, AA1), 4.72 and 4.87 (2H, ABq, J19 Hz), 5.44(1H,s), 6.88(1H,s), 7.1-7.7(14H,m). The salt was suspended in ethyl acetate, treated with dilute sodium hydrogencarbonate solution and the organic phase separated, washed with brine, dried and evaporated to give the title compound (253 mg; 80%). νmax (CHCl3 ) 3375, 1785, 1720, 1625 cm-1 ; δppm (CDCl3) 2.09 (2H, broad s), 2.33 (3H,s), 3.85(3H,s), 4.30(2H,AA1), 4.63 and 4.80 (2H,ABq, J18.8 Hz), 4.88(1H,s), 6.92(1H,s), 7.2-7.6 (10H,m).

Workup

  1. customthe precipitation of the product, which
  2. filtrationwas filtered off
  3. washwashed well with ethyl acetate, ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-f508b19eee5d43d2a2ba5bf5b6940447
Source dataset
uspto-grants-1987_04
Patent number
US04661480

Reaction notes

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