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

HRID 615806Notes

Reaction equation

HRID 615806 reaction equation
[CH:1]([C:3]1[S:4][C:5]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[N:11]=1)=[O:2].[CH3:12][O:13]/[N:14]=[C:15](/[C:46]1[N:47]=[C:48]([NH:51]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:49][CH:50]=1)\[C:16]([NH:18][CH:19]1[C:44](=[O:45])[N:21]2[C:22]([C:28]([O:30]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:29])=[C:23]([CH2:26]I)[CH2:24][S:25][C@H:20]12)=[O:17].CS(C)=O.C(O)(C(F)(F)F)=O>C(OCC)(=O)C.CCOCC.C1(OC)C=CC=CC=1>[NH2:51][C:48]1[S:49][CH:50]=[C:46](/[C:15](=[N:14]/[O:13][CH3:12])/[C:16]([NH:18][CH:19]2[C:44](=[O:45])[N:21]3[C:22]([C:28]([O-:30])=[O:29])=[C:23]([CH2:26][N+:11]4[C:6]5[CH:7]=[N:8][CH:9]=[CH:10][C:5]=5[S:4][C:3]=4[CH:1]=[O:2])[CH2:24][S:25][C@H:20]23)=[O:17])[N:47]=1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 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 15593552Thiazolo[4,5-c]pyridine-2-carbaldehyde

Product 1

HCID 177732399(6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(2-formyl-[1,3]thiazolo[4,5-c]pyridin-3-ium-3-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 101.1%

Reagents, catalysts & solvents 3

HCID 7519AnisoleCatalystHCID 8857Ethyl AcetateCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-formylthiazolo[4,5-c]pyridine (85 mg, 0.5 mmole) and diphenylmethyl 7-[(Z)-2-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-iodomethyl-3-cephem-4-carboxylate [VIIa] (466 mg, 0.5 mmole) in 5 ml of ethyl acetate containing 2 drops of DMSO was allowed to stand overnight at room temperature and then diluted with ether to give 418 mg of crude quaternary salt. The salt was treated with 3 ml of TFA and 3 drops of anisole at room temperature for 30 minutes. The mixture was concentrated in vacuo and triturated with ether to give 283 mg of powder, which was purified by a column of packing (20 ml) in PrepPAK/C18 cartridge (for Water's System 500) using 200 ml of water and 5% aqueous CH3OH (200 ml) as eluants to give 55 mg (20%) of the title compound Iw. Mp. 135°~139° C. (dec.). Estimated purity by HPLC: 55%.

Workup

  1. customto give 418 mg of crude quaternary salt
  2. concentrationThe mixture was concentrated in vacuo
  3. customtriturated with ether

Sources & evidence

ORD record
ord-7c9cc78f59cf4d57b6e5fed25e0ed10f
Source dataset
uspto-grants-1985_02
Patent number
US04500526

Reaction notes

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