Hydrochloric Acid → HCID 178474913, compound

HRID 1707482Notes

Reaction equation

HRID 1707482 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:62])[C@@H:24]([NH:25][C:26](=[O:61])/[C:27](/[C:48]4[N:49]=[C:50]([NH:53]C(OC(C)(C)C)=O)[S:51][CH:52]=4)=[N:28]\[O:29][C:30]([C:32]([O:34]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:33])=[CH2:31])[C@H:21]3[S:20][CH2:19][C:18]=2[S:63][CH:64](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:65][C:66]2[N:67]=[N:68][NH:69][CH:70]=2)=[O:16])C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1(OC)C=CC=CC=1.[N+](C)([O-])=O.O>[NH2:53][C:50]1[S:51][CH:52]=[C:48](/[C:27](=[N:28]/[O:29][C:30]([C:32]([OH:34])=[O:33])=[CH2:31])/[C:26]([NH:25][C@@H:24]2[C:23](=[O:62])[N:22]3[C:17]([C:15]([OH:16])=[O:14])=[C:18]([S:63][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:61])[N:49]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 88300750HCID 88300750, compound

Product 1

HCID 178474913HCID 178474913, compoundYield 77.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6375NitromethaneSolventHCID 7519AnisoleSolvent2×

Procedure

To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-(1-diphenylmethoxycarbonylvinyloxyimino)acetamido]-3-(trityl-1,2,3-triazol-4-ylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester (910 mg: 0.723 mMol.) in a mixture of anisole (3 ml) and nitromethane (12 ml) at -40° C. is added a solution of aluminum chloride (0.77 g: 5.79 mMol.) in anisole (3 ml), and the mixture is stirred at -30° to -40° C. for 50 minutes. The reaction mixture is mixed with 1N-hydrochloric acid (5.8 ml), diluted with water, washed with ethyl acetate, and concentrated under reduced pressure to remove the remaining organic solvents. The resulting aqueous solution is subjected to chromatography over styrene divinylbenzene copolymer (methanol: water=4:1), and resulting powder is washed with ethyl acetate to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-(1-carboxyvinyloxyimino)acetamido]-3-(1,2,3-triazol-4-ylthiomethylthio)-3-cephem-4-carboxylic acid (326 mg) as pale yellow white powder. Yield: 77%.

Workup

  1. washwashed with ethyl acetate
  2. concentrationconcentrated under reduced pressure
  3. customto remove the remaining organic solvents
  4. customresulting powder
  5. washis washed with ethyl acetate

Sources & evidence

ORD record
ord-edcb1fbf31b242a5b4dc88f29242f5fa
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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