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

HRID 615797Notes

Reaction equation

HRID 615797 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][NH:61][C:62](=[O:73])[NH:63][C:64]1[S:65][C:66]2[CH:71]=[CH:70][N:69]=[CH:68][C:67]=2[N:72]=1.C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1>CN(C=O)C.CCOCC.C([O-])(=O)C>[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+:69]4[CH:70]=[CH:71][C:66]5[S:65][C:64]([NH:63][C:62]([NH:61][CH3:60])=[O:73])=[N:72][C:67]=5[CH:68]=4)[CH2:13][S:14][C@H:9]23)=[O:6])[N:36]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 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 155935472-(3-Methylureido)thiazolo[4,5-c]pyridine

Product 1

HCID 177740057(6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[[2-(methylcarbamoylamino)-[1,3]thiazolo[4,5-c]pyridin-5-ium-5-yl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 100.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226428Ether acetateSolvent

Procedure

A mixture of diphenylmethyl 7-[(Z)-2-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-iodomethyl-3-cephem-4-carboxylate [VIIa] (466 mg, 0.5 mmole) and 2-(3-methylureido)-thiazolo[4,5-c]pyridine (104 mg, 0.5 mmole) in 3 ml of dry DMF was stirred at room temperature for 1 hour and diluted with ether acetate to give 430 mg of crude quaternary salt, which was treated with TFA and anisole at room temperature for 30 minutes. The mixture was evaporated and triturated with ether to give 302 mg of crude Ir which was purified on a column of HP-20 resin (40 ml) using 30% CH3OH as an eluant to give 169 mg (56%) of Ir. Mp. 184°~200° C. (dec.). Estimated purity by HPLC: 40%.

Workup

  1. customto give 430 mg of crude quaternary salt, which
  2. customThe mixture was evaporated
  3. customtriturated with ether

Sources & evidence

ORD record
ord-a46b1601d1794ddeadfbebab7cb5a24b
Source dataset
uspto-grants-1985_02
Patent number
US04500526

Reaction notes

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