Hydrochloric Acid → HCID 178477303, compound

HRID 1707488Notes

Reaction equation

HRID 1707488 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:63])[C@@H:24]([NH:25][C:26](=[O:62])/[C:27](/[C:49]4[N:50]=[C:51]([NH:54]C(OC(C)(C)C)=O)[S:52][CH:53]=4)=[N:28]\[O:29]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C@H:21]3[S:20][CH2:19][C:18]=2[S:64][CH:65]([S:67][C:68]2[N:72]=[CH:71][NH:70][N:69]=2)[CH3:66])=[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>[NH2:54][C:51]1[S:52][CH:53]=[C:49](/[C:27](=[N:28]/[OH:29])/[C:26]([NH:25][C@@H:24]2[C:23](=[O:63])[N:22]3[C:17]([C:15]([OH:16])=[O:14])=[C:18]([S:64][CH:65]([S:67][C:68]4[N:72]=[CH:71][NH:70][N:69]=4)[CH3:66])[CH2:19][S:20][C@H:21]23)=[O:62])[N:50]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 178477300HCID 178477300, compound

Product 1

HCID 178477303HCID 178477303, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6375NitromethaneSolventHCID 7519AnisoleSolvent2×

Procedure

To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetylamino]-3-(1-methyl-1,2,4-triazol-3-ylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester (1.52 g: 1.47 mMol.) in a mixture of anisole (5 ml) and nitromethane (20 ml) at -40° C. is added a solution of aluminum chloride (1.56 g: 11.7 mMol.) in anisole (5 ml), and the mixture is stirred at -30° to -40° C. for 1 hour. The reaction mixture is mixed with 1N-hydrochloric acid (12 ml), diluted with water, washed with ethyl acetate, concentrated to remove remaining organic solvents, and passed through a column of styrene-divinylbenzene copolymer adsorbent. The adsorbed product is eluted with water-methanol (1:4). The eluate is concentrated to give powder and washed with ethyl acetate to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetylamino]-3-(1-methyl-1,2,4-triazol-3-ylthiomethylthio)-3-cephem-4-carboxylic acid (628 mg) as yellow powder. Yield: 81%.

Workup

  1. washwashed with ethyl acetate
  2. concentrationconcentrated
  3. customto remove
  4. washThe adsorbed product is eluted with water-methanol (1:4)
  5. concentrationThe eluate is concentrated
  6. customto give powder
  7. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-cc064135feb9418a94bf8cf7ed9eefcc
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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