Aluminum(III) Chloride → HCID 178508516, compound

HRID 1707474Notes

Reaction equation

HRID 1707474 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[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>[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:14])=[S:16])=[C:18]([CH2:64][S:65][C:66]4[N:67]=[N:68][NH:69][CH:70]=4)[CH2:19][S:20][C@H:21]23)=[O:62])[N:50]=1

Participants

5

Reactant 2

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

Product 1

HCID 178508516HCID 178508516, compoundYield 93.4%

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-e6bed7ea83814f6899f3677782e7ee1f
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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