Hydrochloric Acid → HCID 178460213, compound

HRID 1707483Notes

Reaction equation

HRID 1707483 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:54])[C@@H:24]([NH:25][C:26](=[O:53])/[C:27](/[C:40]4[N:41]=[C:42]([NH:45]C(OC(C)(C)C)=O)[S:43][CH:44]=4)=[N:28]\[O:29][C:30]([C:33]([O:35]C(C)(C)C)=[O:34])([CH3:32])[CH3:31])[C@H:21]3[S:20][CH2:19][C:18]=2[S:55][CH:56](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:57][C:58]2[N:59]=[N:60][NH:61][CH:62]=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>[NH2:45][C:42]1[S:43][CH:44]=[C:40](/[C:27](=[N:28]/[O:29][C:30]([C:33]([OH:35])=[O:34])([CH3:31])[CH3:32])/[C:26]([NH:25][C@@H:24]2[C:23](=[O:54])[N:22]3[C:17]([C:15]([OH:16])=[O:14])=[C:18]([S:55][CH2:56][S:57][C:58]4[N:59]=[N:60][NH:61][CH:62]=4)[CH2:19][S:20][C@H:21]23)=[O:53])[N:41]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 178452990HCID 178452990, compound

Product 1

HCID 178460213HCID 178460213, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6375NitromethaneSolventHCID 7519AnisoleSolvent2×

Procedure

To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-(1-t-butoxycarbonyl-1-methylethoxyimino)acetamido]-3-(trityl-1,2,3-triazol-4-ylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester (822 mg: 0.706 mMol.) in a mixture of anisole (3 ml) and nitro- methane (12 ml) at -40° C. is added a solution of aluminum chloride (0.75 g: 5.64 mMol.) in anisole (3 ml), and the mixture is stirred at -30° to -40° C. for 1 hour. The reaction mixture is mixed with 1N-hydrochloric acid (5.7 ml), diluted with water, washed with ethyl acetate, and concentrated under reduced pressure to remove remaining organic solvents. The residual 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-carboxy-1-methylethoxyimino)acetamido]-3-(1,2,3-triazol-4-ylthiomethylthio)-3-cephem-4-carboxylic acid (299 mg) as pale yellowish white powder. Yield: 71%.

Workup

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

Sources & evidence

ORD record
ord-fd421fbcd4874d14839078ebfab0dea8
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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