Formic Acid → HCID 131715187, compound

HRID 652809Notes

Reaction equation

HRID 652809 reaction equation
N[C@@H]1C(=O)N2C(C(OCC3C=CC=CC=3)=O)=C(OS(C(F)(F)F)(=O)=O)CC[C@H]12.C(N(CC)CC)C.C1(C([NH:55][C:56]2[S:57][CH:58]=[C:59]([C:61](=[N:92][O:93][CH3:94])[C:62]([NH:64][C@@H:65]3[C:90](=[O:91])[N:67]4[C:68]([C:80]([O:82]CC5C=CC=CC=5)=[O:81])=[C:69]([O:72][S:73]([C:76]([F:79])([F:78])[F:77])(=[O:75])=[O:74])[CH2:70][CH2:71][C@H:66]34)=[O:63])[N:60]=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)=O>C(#N)C>[NH2:55][C:56]1[S:57][CH:58]=[C:59]([C:61](=[N:92][O:93][CH3:94])[C:62]([NH:64][C@@H:65]2[C:90](=[O:91])[N:67]3[C:68]([C:80]([OH:82])=[O:81])=[C:69]([O:72][S:73]([C:76]([F:78])([F:77])[F:79])(=[O:74])=[O:75])[CH2:70][CH2:71][C@H:66]23)=[O:63])[N:60]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 88599723HCID 88599723, compoundHCID 131715188HCID 131715188, compound

Product 1

HCID 131715187HCID 131715187, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

syn-2-(2-Triphenylmethylthiazol-4-yl)-2-methoxyiminoacetyl chloride is reacted in acetonitrile with benzyl 7β-amino-3-trifluoromethylsulfonyloxy-1-carba-3-cephem-4-carboxylate in the presence of triethylamine and the acylation product, benzyl 7β-[2-(2-triphenylmethylaminothiazol-4-yl)-2-methoxyiminoacetylamino]-3-trifluoromethylsulfonyloxy-1-carba-3-cephem-4-carboxylate is treated with formic acid to remove the triphenylmethyl group and with aluminum chloride in anisole to remove the benzyl ester group to provide the title compound.

Workup

  1. customto remove the triphenylmethyl group
  2. customwith aluminum chloride in anisole to remove the benzyl ester group

Sources & evidence

ORD record
ord-e2e25bfa5e474229aa53a1986a5af731
Source dataset
uspto-grants-1987_06
Patent number
US04673737

Reaction notes

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