Aluminum(III) Chloride → HCID 9826491, compound

HRID 992708Notes

Reaction equation

HRID 992708 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[NH2:5][C:6]1[S:7][CH:8]=[C:9](/[C:11](=[N:66]/[O:67]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)/[C:12]([NH:14][C@@H:15]2[C:64](=[O:65])[N:17]3[C:18]([C:48]([O:50]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:49])=[C:19]([S:22][CH2:23][C:24]4[CH:25]=[N:26][N:27](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:28]=4)[CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1>C1(OC)C=CC=CC=1.[N+](C)([O-])=O>[NH2:5][C:6]1[S:7][CH:8]=[C:9](/[C:11](=[N:66]/[OH:67])/[C:12]([NH:14][C@@H:15]2[C:64](=[O:65])[N:17]3[C:18]([C:48]([OH:50])=[O:49])=[C:19]([S:22][CH2:23][C:24]4[CH:25]=[N:26][NH:27][CH:28]=4)[CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1

Participants

5

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 16147301benzhydryl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-trityloxyiminoacetyl]amino]-8-oxo-3-[(1-tritylpyrazol-4-yl)methylsulfanyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 9826491HCID 9826491, compound

Reagents, catalysts & solvents 2

HCID 6375NitromethaneSolventHCID 7519AnisoleSolvent2×

Procedure

Under nitrogen atomosphere, a solution of aluminium chloride (2.65 g) in anisole (5.7 ml) was added dropwise to a solution of diphenylmethyl 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(trityloxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate (3.32 g) in a mixture of anisole (5.7 ml) and nitromethane (22.5 ml) at −24° C. After stirring for 1 hour at the same temperature, the reaction was quenched with 1N hydrochloric acid (22.5 ml). The mixture was poured into a mixture of water and ethyl acetone. The aqueous layer was separated and the organic layer was reextracted with water. The combined aqueous layer was concentrated in vacuo, chromatographed on a HP-20 column (eluent: water-methanol). After the concentration, the resulting precipitate was collected by filtration to afford 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(hydroxyimino)acetamido]-3-[(pyrazol-4-yl)methylthio]-3-cephem-4-carboxylic acid

Workup

  1. customthe reaction was quenched with 1N hydrochloric acid (22.5 ml)
  2. additionThe mixture was poured into a mixture of water and ethyl acetone
  3. customThe aqueous layer was separated
  4. concentrationThe combined aqueous layer was concentrated in vacuo
  5. customchromatographed on a HP-20 column (eluent: water-methanol)
  6. concentrationAfter the concentration
  7. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-2ee7f2a8a8c44736b24679682d334a55
Source dataset
uspto-grants-2002_10
Patent number
US06468995B1

Reaction notes

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