Trifluoroacetic acid → (6R)-3-[[2-[(2-aminoacetyl)amino]-[1,3]thiazolo[4,5-c]pyridin-5-ium-5-yl]methyl]-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 615795Notes

Reaction equation

HRID 615795 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].C(OC([NH:67][CH2:68][C:69]([NH:71][C:72]1[S:73][C:74]2[CH:79]=[CH:78][N:77]=[CH:76][C:75]=2[N:80]=1)=[O:70])=O)(C)(C)C.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+:77]4[CH:78]=[CH:79][C:74]5[S:73][C:72]([NH:71][C:69](=[O:70])[CH2:68][NH2:67])=[N:80][C:75]=5[CH:76]=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 155935462-(N-t-Butoxycarbonylglycylamino)thiazolo[4,5-c]pyridine

Product 1

HCID 177727401(6R)-3-[[2-[(2-aminoacetyl)amino]-[1,3]thiazolo[4,5-c]pyridin-5-ium-5-yl]methyl]-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 96%

Reagents, catalysts & solvents 3

HCID 7519AnisoleCatalystHCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of diphenylmethyl 7-[(Z)-2-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-iodomethyl-3-cephem-4-carboxylate [VIIa] (237 mg, 0.29 mmole) and 2-(N-t-butoxycarbonylglycylamino)thiazolo[4,5-c]pyridine (95 mg, 0.31 mmole) in 2 ml of dry DMSO was allowed to stand at room temperature for 2 hours and then diluted with ether to give the crude quaternary salt, which was treated with 90% TFA and 2 drops of anisole at room temperature for 30 minutes. The mixture was evaporated and triturated with ether to afford 168 mg of pale yellow precipitate, which was purified by a column of HP-20 resin (40 ml) using 30% aqueous CH3OH as an eluant to give 88 mg of the title product Iq. Mp. 178°-187° C. (dec.). Estimated purity by HPLC: 60%.

Workup

  1. customto give the crude quaternary salt, which
  2. customThe mixture was evaporated
  3. customtriturated with ether

Sources & evidence

ORD record
ord-b56af48724d74febaa9500672fbe51d4
Source dataset
uspto-grants-1985_02
Patent number
US04500526

Reaction notes

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