Hydrochloric Acid → HCID 178508494, compound

HRID 1707476Notes

Reaction equation

HRID 1707476 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:49])[C@@H:24]([NH:25][C:26](=[O:48])/[C:27](/[C:35]4[N:36]=[C:37]([NH:40]C(OC(C)(C)C)=O)[S:38][CH:39]=4)=[N:28]\[O:29][CH:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)[C@H:21]3[S:20][CH2:19][C:18]=2[S:50][CH2:51][S:52][C:53]2[N:54]=[N:55][NH:56][CH:57]=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>[NH2:40][C:37]1[S:38][CH:39]=[C:35](/[C:27](=[N:28]/[O:29][CH:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)/[C:26]([NH:25][C@@H:24]2[C:23](=[O:49])[N:22]3[C:17]([C:15]([OH:16])=[O:14])=[C:18]([S:50][CH2:51][S:52][C:53]4[N:54]=[N:55][NH:56][CH:57]=4)[CH2:19][S:20][C@H:21]23)=[O:48])[N:36]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 178452984HCID 178452984, compound

Product 1

HCID 178508494HCID 178508494, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6375NitromethaneSolventHCID 7519AnisoleSolvent2×

Procedure

To a suspension of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-cyclopentyloxyiminoacetamido]-3-(1,2,3-triazol-4-ylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester (258 mg: 0.304 mMol.) in a mixture of anisole (1 ml) and nitromethane (4 ml) at -30° C. is added a solution of aluminum chloride (0.25 g: 1.88 mMol.) in anisole (1 ml), and the mixture is stirred for 50 minutes. The reaction mixture is diluted with ethanol (2 ml), stirred at the same temperature for 5 minutes, mixed with 1N-hydrochloric acid (4 ml) and water (200 ml), and stirred at room temperature for 5 minutes. The aqueous layer is taken, washed with ethyl acetate, concentrated under reduced pressure to remove remaining organic solvents, and subjected to chromatography over styrene-divinylbenzene copolymer (methanol : water=4:1) to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-cyclopentyloxyiminoacetamido]-3-(1,2,3-triazol-4-ylthiomethylthio)-3-cephem-4-carboxylic acid (93 mg) as white solid. Yield: 53%.

Workup

  1. stirringstirred at the same temperature for 5 minutes
  2. stirringstirred at room temperature for 5 minutes
  3. washwashed with ethyl acetate
  4. concentrationconcentrated under reduced pressure
  5. customto remove

Sources & evidence

ORD record
ord-0e4a07ddb9574391a0c5d71a5f9e99ba
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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