Hydrochloric Acid → HCID 178447402, compound

HRID 1707473Notes

Reaction equation

HRID 1707473 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:45])[C@@H:24]([NH:25][C:26](=[O:44])/[C:27](/[C:31]4[N:32]=[C:33]([NH:36]C(OC(C)(C)C)=O)[S:34][CH:35]=4)=[CH:28]\[CH2:29][CH3:30])[C@H:21]3[S:20][CH2:19][C:18]=2[S:46][CH2:47][S:48][C:49]2[N:50]=[N:51][NH:52][CH:53]=2)=[O:16])C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl.O>C1(OC)C=CC=CC=1.[N+](C)([O-])=O.C(O)C>[NH2:36][C:33]1[S:34][CH:35]=[C:31](/[C:27](=[CH:28]/[CH2:29][CH3:30])/[C:26]([NH:25][C@@H:24]2[C:23](=[O:45])[N:22]3[C:17]([C:15]([OH:16])=[O:14])=[C:18]([S:46][CH2:47][S:48][C:49]4[N:50]=[N:51][NH:52][CH:53]=4)[CH2:19][S:20][C@H:21]23)=[O:44])[N:32]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 178447401HCID 178447401, compound

Product 1

HCID 178447402HCID 178447402, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6375NitromethaneSolventHCID 7519AnisoleSolvent2×

Procedure

To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino]-3-(1,2,3-triazol-4-ylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester (537 mg: 0.68 mMol.) in a mixture of anisole (2 ml) and nitromethane (8 ml) at -30° C. is added a solution of aluminum chloride (0.54 g: 4 mMol. ) in anisole (2 ml), and the mixture is stirred for 1 hour. The reaction mixture is diluted with ethanol (3 ml), stirred for 5 minutes, mixed with 1N-hydrochloric acid (8 ml) and water (200 ml), washed with ethyl acetate, and concentrated under reduced pressure to remove remaining organic solvents. The resulting aqueous solution is subjected to chromatography over styrene-divinylbenzene copolymer (methanol: water=4:1) to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-pentenoylamino]-3-(1,2,3-triazol-4-ylthiomethylthio)-3-cephem-4-carboxylic acid (156 mg) as white solid. Yield: 44%.

Workup

  1. stirringstirred for 5 minutes
  2. washwashed with ethyl acetate
  3. concentrationconcentrated under reduced pressure
  4. customto remove

Sources & evidence

ORD record
ord-a22b8043f1a04b4aba02fd203526847d
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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