Aluminum(III) Chloride → HCID 178516324, compound

HRID 249617Notes

Reaction equation

HRID 249617 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:63])[C@@H:24](NC(=O)/C(/C4N=C(NC(OC(C)(C)C)=O)SC=4)=N\OC(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C@H:21]3[S:20][CH2:19][C:18]=2[CH2:64][S:65][C:66]2[N:67]=[N:68][NH: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>[NH:69]1[CH:70]=[C:66]([S:65][CH2:64][C:18]2[CH2:19][S:20][C@@H:21]3[CH2:24][C:23](=[O:63])[N:22]3[C:17]=2[C:15]([OH:14])=[S:16])[N:67]=[N:68]1

Participants

5

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 178452987HCID 178452987, compound

Product 1

HCID 178516324HCID 178516324, compoundYield 148.1%

Reagents, catalysts & solvents 2

HCID 6375NitromethaneSolventHCID 7519AnisoleSolvent2×

Procedure

To a suspension of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol -4- yl)-2-trityloxyiminoacetamido]-3-(1,2,3-triazol-4-yl) thiomethylthio-3- cephem-4-carboxylic acid diphenylmethyl ester (9.2 g: 9 mMol.) in a mixture of anisole (18 ml) and nitromethane (72 ml) is added dropwise a solution of aluminum chloride (9.6 g: 72 mMol.) in anisole (31 ml) at -30° C. After stirring for 1 hour at the same temperature, the reaction mixture is quenched with ethanol (25 ml), stirred for several minutes, diluted with 1N-hydrochloric acid (75 ml) and water (500 ml), and washed with ethyl acetate. The aqueous layer was separated, concentrated to remove the organic solvents, and passed through a column of styrene- divinylbenzene copolymer adsorbent. The product is eluted with a mixture of methanol and water (4:1) to give 7β-(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-(1,2,3-triazol-4-yl)thiomethylthio -3-cephem-4-carboxylic acid as pale yellow powder (4.19 g). Yield: 90%.

Workup

  1. customthe reaction mixture is quenched with ethanol (25 ml)
  2. stirringstirred for several minutes
  3. additiondiluted with 1N-hydrochloric acid (75 ml) and water (500 ml)
  4. washwashed with ethyl acetate
  5. customThe aqueous layer was separated
  6. concentrationconcentrated
  7. customto remove the organic solvents
  8. washThe product is eluted with a mixture of methanol and water (4:1)

Sources & evidence

ORD record
ord-c6b8e3efd4634cb9ab33f3af0092d8fd
Source dataset
uspto-grants-1993_05
Patent number
US05214037

Reaction notes

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