Hydrochloric Acid → HCID 178508417, compound

HRID 249620Notes

Reaction equation

HRID 249620 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:42])[C@@H:24]([NH:25][C:26](=[O:41])[CH2:27][C:28]4[N:29]=[C:30]([NH:33]C(OC(C)(C)C)=O)[S:31][CH:32]=4)[C@H:21]3[S:20][CH2:19][C:18]=2[S:43][CH:44](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:45][C:46]2[N:47]=[N:48][NH:49][CH:50]=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>[NH2:33][C:30]1[S:31][CH:32]=[C:28]([CH2:27][C:26]([NH:25][C@@H:24]2[C:23](=[O:42])[N:22]3[C:17]([C:15]([OH:16])=[O:14])=[C:18]([S:43][CH2:44][S:45][C:46]4[N:47]=[N:48][NH:49][CH:50]=4)[CH2:19][S:20][C@H:21]23)=[O:41])[N:29]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 178452982HCID 178452982, compound

Product 1

HCID 178508417HCID 178508417, compoundYield 59.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6375NitromethaneSolventHCID 7519AnisoleSolvent2×

Procedure

To a solution of 7β-[2-(2-t-butoxycarbonylaminothiazol -4-yl)acetamido]-3-(trityl-1,2,3-triazol-4-ylthiomethylthio) -3-cephem-4-carboxylic acid diphenylmethyl ester (779 mg : 0.784 mMol.) in a mixture of anisole (3 ml) and nitromethane (12 ml) at -40° C. is added a solution of aluminum chloride (0.83 g : 6.24 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 (6.3 ml), diluted with water, washed with ethyl acetate, and concentrated under reduced pressure to remove the remaining organic solvents. The residual solution is subjected to the chromatography over styrene-divinylbenzene copolymer (methanol : water=4:1) and resulting powder is washed with ethyl acetate to give 7β-[2- (2-aminothiazol-4yl)acetamido]-3-(1,2,3-triazol-4-ylthiomethylthio)-3-cephem -4-carboxylic acid (225 mg) as white powder. Yield: 59%.

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-f72f36878c51432682c47f85ff5b8e34
Source dataset
uspto-grants-1993_05
Patent number
US05214037

Reaction notes

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