Trifluoroacetic acid → HCID 178502772, compound

HRID 615799Notes

Reaction equation

HRID 615799 reaction equation
[CH3:1][O:2]/[N:3]=[C:4](/[C:35]1[N:36]=[C:37]([NH:40]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:38][CH:39]=1)\[C:5]([NH:7][CH:8]1[C:33](=[O:34])[N:10]2[C:11]([C:17]([O:19]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:18])=[C:12]([CH2:15]I)[CH2:13][S:14][C@H:9]12)=[O:6].[CH3:60][O:61][C:62]([NH:64][C:65]1[S:66][C:67]2[CH:72]=[CH:71][N:70]=[CH:69][C:68]=2[N:73]=1)=[O:63].C(O)(C(F)(F)F)=O>CS(C)=O.CCOCC.C1(OC)C=CC=CC=1>[NH2:40][C:37]1[S:38][CH:39]=[C:35](/[C:4](=[N:3]/[O:2][CH3:1])/[C:5]([NH:7][CH:8]2[C:33](=[O:34])[N:10]3[C:11]([C:17]([O-:19])=[O:18])=[C:12]([CH2:15][N+:70]4[CH:71]=[CH:72][C:67]5[S:66][C:65]([NH:64][C:62]([O:61][CH3:60])=[O:63])=[N:73][C:68]=5[CH:69]=4)[CH2:13][S:14][C@H:9]23)=[O:6])[N:36]=1

Participants

7

Reactant 3

HCID 6422Trifluoroacetic acidHCID 13239634benzhydryl (6R)-3-(iodomethyl)-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 155935482-Methoxycarbonylaminothiazolo[4,5-c]pyridine

Product 1

HCID 178502772HCID 178502772, compound

Reagents, catalysts & solvents 3

HCID 7519AnisoleCatalystHCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of diphenylmethyl 7-[(Z)-2-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-iodomethyl-3-cephem-4-carboxylate [VIIa] (419 mg, 0.45 mmole) and 2-methoxycarbonylaminothiazolo[4,5-c]pyridine (94 mg, 0.45 mmole) in 2 ml of dry DMSO was allowed to stand at room temperature for 1 hour and diluted with ether to give 514 mg of crude quaternary salt, which was treated with 5 ml of TFA and 3 drops of anisole at room temperature for 30 minutes. The mixture was evaporated in vacuo and triturated with ether to afford 338 mg of crude Is which was purified on a column of HP-20 resin (40 ml) using 30% aqueous CH3OH as an eluant to give 95 mg (35%) of Is. Mp. 156°~184° C. (dec.). Estimated purity by HPLC: 40%.

Workup

  1. customto give 514 mg of crude quaternary salt, which
  2. customThe mixture was evaporated in vacuo
  3. customtriturated with ether
  4. customto afford 338 mg of crude
  5. customwas purified on a column of HP-20 resin (40 ml)
  6. customto give 95 mg (35%) of Is

Sources & evidence

ORD record
ord-4722ab0c5e45493cba1cf36bf6d5137b
Source dataset
uspto-grants-1985_02
Patent number
US04500526

Reaction notes

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