Aluminum(III) Chloride → HCID 178481984, compound

HRID 249621Notes

Reaction equation

HRID 249621 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:25])[CH2:24][C@H:21]3[S:20][C:19](NC(=O)/C=N\OC(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)(C3N=C(NC(OC(C)(C)C)=O)SC=3)[C:18]=2[CH2:64][S:65][C:66]2[N:67]([CH3:71])[N:68]=[N:69][CH:70]=2)=[S: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>[CH3:71][N:67]1[C:66]([S:65][CH2:64][C:18]2[CH2:19][S:20][C@@H:21]3[CH2:24][C:23](=[O:25])[N:22]3[C:17]=2[C:15]([OH:14])=[S:16])=[CH:70][N:69]=[N:68]1

Participants

7

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 178481986HCID 178481986, compound

Product 1

HCID 178481984HCID 178481984, compoundYield 128.2%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6375NitromethaneSolventHCID 7519AnisoleSolvent2×

Procedure

To a solution of 7μ-[(Z)-2-(2-t-butoxycarbonylaminothiazol -4-yl)- 2-trityloxyiminoacetamido-3-(3-methyl-1,2,3-triazol-4-yl)thiomethylthio-3-cephem-4-carboxylic acid diphenylmethyl ester (900 mg: 0.869 mMol.) in a mixture of anisole (4 ml) and nitromethane (16 ml) is added a solution of aluminum chloride (924 mg: 6.95 mMol.) in anisole (2 ml) at -40° C., and the mixture is stirred for 1 hour at -40°-30° C. The reaction mixture is diluted with 1N-hydrochloric acid (7 ml) and water and washed with ethyl acetate. The aqueous layer is concentrated under reduced pressure to remove organic solvent and passed through a column of styrene-divinylbenzene copolymer adsorbent. The product is eluted with methanol-water (4:1) to give 7μ-(Z)-2-(2-aminothiazol -4-yl)-2-hydroxyiminoacetamido]-3-(3-methyl-1,2,3-triazol-4-yl)thiomethylthio-3-cephem-4-carboxylic acid as pale yellow powder (366 mg). Yield: 80%.

Workup

  1. washwashed with ethyl acetate
  2. concentrationThe aqueous layer is concentrated under reduced pressure
  3. customto remove organic solvent
  4. washThe product is eluted with methanol-water (4:1)

Sources & evidence

ORD record
ord-d90f0393aaa4433ba9d7ac65c4203e03
Source dataset
uspto-grants-1993_05
Patent number
US05214037

Reaction notes

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