Propylene Oxide → HCID 88835316, compound

HRID 1287593Notes

Reaction equation

HRID 1287593 reaction equation
S1C=CC=C1CC(NC1C(=O)N2C(C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)=C(O)CS[C@H]12)=O.FC1C=CC(S(Cl)(=O)=O)=CC=1.C1OC1C.[S:48]1[CH:52]=[CH:51][CH:50]=[C:49]1[CH2:53][C:54]([NH:56][CH:57]1[C:88](=[O:89])[N:59]2[C:60]([C:75]([O:77]CC3C=CC([N+]([O-])=O)=CC=3)=[O:76])=[C:61]([O:64][S:65]([C:68]3[CH:73]=[CH:72][C:71]([F:74])=[CH:70][CH:69]=3)(=[O:67])=[O:66])[CH2:62][S:63][C@H:58]12)=[O:55]>CC(N(C)C)=O.CO.C1COCC1.[Pd]>[S:48]1[CH:52]=[CH:51][CH:50]=[C:49]1[CH2:53][C:54]([NH:56][CH:57]1[C:88](=[O:89])[N:59]2[C:60]([C:75]([OH:77])=[O:76])=[C:61]([O:64][S:65]([C:68]3[CH:73]=[CH:72][C:71]([F:74])=[CH:70][CH:69]=3)(=[O:67])=[O:66])[CH2:62][S:63][C@H:58]12)=[O:55]

Participants

8

Reactant 4

HCID 6378Propylene OxideHCID 95884-Fluorobenzenesulfonyl chlorideHCID 70559815p-Nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-hydroxy-3-cephem-4-carboxylateHCID 88835879HCID 88835879, compound

Product 1

HCID 88835316HCID 88835316, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 31374DimethylacetamideSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

By following the sulfonation and de-esterification procedures described in Example 4 p-nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-hydroxy-3-cephem-4-carboxylate was reacted with 4-fluorobenzenesulfonyl chloride in DMAC in the presence of propylene oxide and the recovered sulfonation product, p-nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-(4-fluorobenzenesulfonyloxy)-3-cephem-4-carboxylate was hydrogenated in methanol-THF over prereduced 5 percent palladium on carbon catalyst to provide the product, 7-[2-(2-thienyl)acetamido]-3-(4-fluorobenzenesulfonyloxy)-3-cephem-4-carboxylic acid.

Sources & evidence

ORD record
ord-9fb8932102e94f29a54cc943c07535ef
Source dataset
uspto-grants-1976_10
Patent number
US03985737

Reaction notes

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