p-Toluenesulfonic acid monohydrate → HCID 178494568, compound

HRID 1082748Notes

Reaction equation

HRID 1082748 reaction equation
[NH2:1][CH:2]1[C:24](=[O:25])[N:4]2[C:5]([C:12]([O:14][C@H:15]([O:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[CH3:16])=[O:13])=[C:6]([CH2:9][O:10][CH3:11])[CH2:7][S:8][C@@H:3]12.[NH2:26][C:27]1[S:28][CH:29]=[C:30](/[C:32](=[N:45]/[O:46]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)/[C:33]([O:35]C2SC3C=CC=CC=3N=2)=S)[N:31]=1.O.[C:67]1([CH3:77])[CH:72]=[CH:71][C:70]([S:73]([OH:76])(=[O:75])=[O:74])=[CH:69][CH:68]=1>CN(C)C=O.C(O)CC>[C:67]1([CH3:77])[CH:68]=[CH:69][C:70]([S:73]([OH:76])(=[O:74])=[O:75])=[CH:71][CH:72]=1.[NH2:26][C:27]1[S:28][CH:29]=[C:30](/[C:32](=[N:45]/[OH:46])/[C:33]([NH:1][CH:2]2[C:24](=[O:25])[N:4]3[C:5]([C:12]([O:14][C@H:15]([O:17][C:18]([O:20][CH:21]([CH3:22])[CH3:23])=[O:19])[CH3:16])=[O:13])=[C:6]([CH2:9][O:10][CH3:11])[CH2:7][S:8][C@@H:3]23)=[O:35])[N:31]=1

Participants

6

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 73357601HCID 73357601, compoundHCID 131719761HCID 131719761, compound

Product 1

HCID 178494568HCID 178494568, compound

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 6228DimethylformamideSolvent

Procedure

905 mg (2.42 mmol) of 1-(1R,S)-(isopropyloxycarbonyloxy)ethyl 7-amino-3-methoxymethyl-3-cephem-4-carboxylate and 1.5 g (2.6 mmol) of 2-benzothiazolyl (Z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminothioacetate are reacted in 10 ml of N,N-dimethylformamide analogously to Example 5. The trityl-protected title compound is heated at 90° C. for 25 minutes with 475 mg (2.5 mmol) of p-toluenesulfonic acid hydrate in 10 ml of n-propanol. After cooling, 900 mg (52% of theory) of the title compound crystallize. If the trityl group is first removed with formic acid and the tosylate is then formed analogously to Example 5, the yield is 231 mg (13% of theory).

Sources & evidence

ORD record
ord-94497a488f5b48cbb2227918d4df7eb1
Source dataset
uspto-grants-1996_12
Patent number
US05589594

Reaction notes

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