Formic Acid → HCID 131715187, compound

HRID 620383Notes

Reaction equation

HRID 620383 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(C2C=CC=CC=2)(C2C=CC=CC=2)C[NH:44][C:45]2[S:46][CH:47]=[C:48]([C:50](=[N:81][O:82][CH3:83])[C:51]([NH:53][C@@H:54]3[C:79](=[O:80])[N:56]4[C:57]([C:69]([O:71]CC5C=CC=CC=5)=[O:70])=[C:58]([O:61][S:62]([C:65]([F:68])([F:67])[F:66])(=[O:64])=[O:63])[CH2:59][CH2:60][C@H:55]34)=[O:52])[N:49]=2)C=CC=CC=1.C(O)=O>C(#N)C>[NH2:44][C:45]1[S:46][CH:47]=[C:48]([C:50](=[N:81][O:82][CH3:83])[C:51]([NH:53][C@@H:54]2[C:79](=[O:80])[N:56]3[C:57]([C:69]([OH:71])=[O:70])=[C:58]([O:61][S:62]([C:65]([F:67])([F:66])[F:68])(=[O:63])=[O:64])[CH2:59][CH2:60][C@H:55]23)=[O:52])[N:49]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 88599723HCID 88599723, compoundHCID 131715917HCID 131715917, 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-triphenylethylaminothiazol-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 ih anisole to remove the benzyl ester group to provide the title compound.

Workup

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

Sources & evidence

ORD record
ord-ed031cf11433402cbfa662266954f9f6
Source dataset
uspto-grants-1989_04
Patent number
US04820816

Reaction notes

Loading…