Aluminum(III) Chloride → HCID 88158471, compound

HRID 992706Notes

Reaction equation

HRID 992706 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[NH2:5][C:6]1[S:7][CH:8]=[C:9](/[C:11](=[N:48]/[O:49]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)/[C:12]([NH:14][C@@H:15]2[C:46](=[O:47])[N:17]3[C:18]([C:30]([O:32]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:31])=[C:19]([S:22][CH2:23][C:24]4[S:28][N:27]=[N:26][C:25]=4[CH3:29])[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:48]/[OH:49])/[C:12]([NH:14][C@@H:15]2[C:46](=[O:47])[N:17]3[C:18]([C:30]([OH:32])=[O:31])=[C:19]([S:22][CH2:23][C:24]4[S:28][N:27]=[N:26][C:25]=4[CH3:29])[CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1

Participants

5

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 88158476HCID 88158476, compound

Product 1

HCID 88158471HCID 88158471, compoundYield 10.4%

Reagents, catalysts & solvents 2

HCID 6375NitromethaneSolventHCID 7519AnisoleSolvent2×

Procedure

Under N2 atmosphere, a solution of aluminum chloride (1.88 g, 14.05 m mol) in anisole (4.5 ml) was added slowly to a solution of diphenylmethyl 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(trityloxyimino)acetamido]-3-[(4-methyl-1,2,3-thiadiazol-5-yl)methylthio]-3-cephem-4-carboxylate (2.60 g, 2.81 m mol) in anisole (4.5 ml) and nitromethane (18 ml) at −30˜20° C. After the mixture was stirred for 1 hour at the same temperature, the reaction was quenched with 1N hydrochloric acid (18 ml), and poured into water/ethyl acetate. 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 concentration, the resulting precipitate was collected by filtration, and dried in vacuo to afford 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(hydroxyimino)acetamido]-3-[(4-methyl-1,2,3-thiadiazol-5-yl)methylthio]-3-cephem-4-carboxylic acid (150.8 mg).

Workup

  1. customthe reaction was quenched with 1N hydrochloric acid (18 ml)
  2. additionpoured into water/ethyl acetate
  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 concentration
  7. filtrationthe resulting precipitate was collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-9e0b739092e54ba78ff74d0eae13502d
Source dataset
uspto-grants-2002_10
Patent number
US06468995B1

Reaction notes

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