Hydrochloric Acid → HCID 178508515, compound

HRID 1707469Notes

Reaction equation

HRID 1707469 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:85][CH2:86][C:87]2[N:88]=[N:89][NH:90][CH:91]=2)C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=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>[NH2:54][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][CH2:65][S:85][CH2:86][C:87]4[N:88]=[N:89][NH:90][CH:91]=4)[CH2:19][S:20][C@H:21]23)=[O:62])[N:50]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 141566139HCID 141566139, compound

Product 1

HCID 178508515HCID 178508515, compoundYield 68.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6375NitromethaneSolventHCID 7519AnisoleSolvent2×

Procedure

To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-(1-trityl-1,2,3-triazol-4-ylmethylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester (1.13 g: 0.884 mMol.) in a mixture of anisole (3 ml) and nitromethane (12 ml) at -40° C. is added a solution of aluminum chloride (0.94 g: 7.07 mMol.) in anisole (3 mi), and the mixture is stirred at -30° to -40° C. for 1 hour. The reaction mixture is mixed with 1N-hydrochloric acid (7.5 ml) and diluted with water. The aqueous solution is washed with ethyl acetate. The aqueous layer is concentrated under reduced pressure to remove the remaining organic solvents, subjected to chromatography over styrene-divinylbenzene copolymer column (methanol : water=4:1). The resulting powder is washed with ethyl acetate to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-(1,2,3-triazol-4-ylmethylthiomethylthio)-3-cephem-4-carboxylic acid (318 mg) as pale yellow white powder. Yield: 68%.

Workup

  1. washThe aqueous solution is washed with ethyl acetate
  2. concentrationThe aqueous layer is concentrated under reduced pressure
  3. customto remove the remaining organic solvents
  4. washThe resulting powder is washed with ethyl acetate

Sources & evidence

ORD record
ord-0ad5c3b82bdc4a0ebac3072f78f02bef
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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