Hydrochloric Acid → HCID 178508517, compound

HRID 1707489Notes

Reaction equation

HRID 1707489 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[CH2:64][S:65][C:66]2[S:70][N:69]=[N:68][CH:67]=2)=[S: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:14])=[S:16])=[C:18]([CH2:64][S:65][C:66]4[S:70][N:69]=[N:68][CH:67]=4)[CH2:19][S:20][C@H:21]23)=[O:62])[N:50]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 141566148HCID 141566148, compound

Product 1

HCID 178508517HCID 178508517, compoundYield 73.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6375NitromethaneSolventHCID 7519AnisoleSolvent2×

Procedure

To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetyl]amino-3-(1,2,3-thiadiazol-5-yl) thiomethylthio-3-cephem-4-carboxylic acid diphenylmethyl ester (1.21 g: 1.16 mMol.) in a mixture of anisole (4 ml) and nitromethane (16 ml) cooling at -30° to -40° C. is added a solution of aluminum chloride (1.23 g: 9.25 mMol.) in anisole (4 ml), and the mixture is stirred at -30° to -40° C. for 50 minutes. To the reaction mixture is added 1N-hydrochloric acid (10 ml), diluted with water, and washed with ethyl acetate. The aqueous layer is concentrated to remove the organic solvents, purified by styrene-divinylbenzene copolymer chromatography (methanol: water=4:1) and the resulting powder is washed with ethyl acetate to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetyl]amino-3-(1,2,3-thiadiazol-5-yl)thiomethylthio-3-cephem-4-carboxylic acid as yellow powder (440 mg). Yield 71%.

Workup

  1. temperaturecooling at -30° to -40° C.
  2. washwashed with ethyl acetate
  3. concentrationThe aqueous layer is concentrated
  4. customto remove the organic solvents
  5. custompurified by styrene-divinylbenzene copolymer chromatography (methanol: water=4:1)
  6. washthe resulting powder is washed with ethyl acetate

Sources & evidence

ORD record
ord-53726d64f7a44683b28c24f876957113
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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