Aluminum(III) Chloride → (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-(pyridin-2-ylsulfanylmethylsulfanyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1707495Notes

Reaction equation

HRID 1707495 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:63])[C@@H:24]([NH:25][C:26](=[O:62])/[C:27](/[C:49]4[N:50]=[C:51]([NH:54]C(OC(C)(C)C)=O)[S:52][CH:53]=4)=[N:28]\[O:29]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C@H:21]3[S:20][CH2:19][C:18]=2[S:64][CH2:65][S:66][C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][N:68]=2)=[O:16])C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-]>C1(OC)C=CC=CC=1.[N+](C)([O-])=O.Cl.O>[NH2:54][C:51]1[S:52][CH:53]=[C:49](/[C:27](=[N:28]/[OH:29])/[C:26]([NH:25][C@@H:24]2[C:23](=[O:63])[N:22]3[C:17]([C:15]([OH:16])=[O:14])=[C:18]([S:64][CH2:65][S:66][C:67]4[CH:72]=[CH:71][CH:70]=[CH:69][N:68]=4)[CH2:19][S:20][C@H:21]23)=[O:62])[N:50]=1

Participants

7

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 16143732benzhydryl (6R,7R)-7-[[(2Z)-2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-trityloxyiminoacetyl]amino]-8-oxo-3-(pyridin-2-ylsulfanylmethylsulfanyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 10324526(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-(pyridin-2-ylsulfanylmethylsulfanyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 79%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6375NitromethaneSolventHCID 7519AnisoleSolvent2×

Conditions

Temperature
-40 °C

Procedure

To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-(2-pyridylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester (722 mg: 0.70 mMol.) in a mixture of anisole (2 ml) and nitromethane (8 ml) cooling at -40° C. is added a solution of aluminum chloride (744 mg; 5.59 mMol. ) in anisole (2 ml), and the mixture is stirred at -30° to -40° C. for 1 hour. The reaction mixture is diluted with 1N-hydrochloric acid (6 ml) and water, washed with ethyl acetate, concentrated under reduced pressure to remove the organic solvents, and passed through a styrene-divinylbenzene copolymer column. The adsorbed material is eluted with methanol-water (4:1). The eluate is concentrated. The residue is washed with ethyl acetate and dried to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetylamino]-3-(2-pyridylthiomethylthio)-3-cephem-4-carboxylic acid (289 mg). Yield: 79%.

Workup

  1. washwashed with ethyl acetate
  2. concentrationconcentrated under reduced pressure
  3. customto remove the organic solvents
  4. washThe adsorbed material is eluted with methanol-water (4:1)
  5. concentrationThe eluate is concentrated
  6. washThe residue is washed with ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-459db49e2e3945ca949d6301ff31d725
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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