Hydrochloric Acid → HCID 178460212, compound

HRID 249618Notes

Reaction equation

HRID 249618 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:47])[C@@H:24]([NH:25][C:26](=[O:46])/[C:27](/[C:33]4[N:34]=[C:35]([NH:38]C(OC(C)(C)C)=O)[S:36][CH:37]=4)=[N:28]\[O:29][CH2:30][CH:31]=[CH2:32])[C@H:21]3[S:20][CH2:19][C:18]=2[S:48][CH2:49][S:50][C:51]2[N:52]=[N:53][NH:54][CH:55]=2)=[O:16])C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].C(O)C.Cl>C1(OC)C=CC=CC=1.[N+](C)([O-])=O.O>[NH2:38][C:35]1[S:36][CH:37]=[C:33](/[C:27](=[N:28]/[O:29][CH2:30][CH:31]=[CH2:32])/[C:26]([NH:25][C@@H:24]2[C:23](=[O:47])[N:22]3[C:17]([C:15]([OH:16])=[O:14])=[C:18]([S:48][CH2:49][S:50][C:51]4[N:52]=[N:53][NH:54][CH:55]=4)[CH2:19][S:20][C@H:21]23)=[O:46])[N:34]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6451240Aluminum(III) ChlorideHCID 178460211HCID 178460211, compound

Product 1

HCID 178460212HCID 178460212, compoundYield 49.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6375NitromethaneSolventHCID 7519AnisoleSolvent2×

Procedure

To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol -4-yl)- 2-(2-propenyloxyimino)acetamido]-3-(1,2,3-triazol-4-ylthiomethylthio)-3- cephem-4-carboxylic acid diphenylmethyl ester (376 mg : 0.46 mMol.) in a mixture of anisole (1.5 ml) and nitromethane (6 ml) at -30° C. is added a solution of aluminum chloride (0.37 g : 2.8 mMol.) in anisole (1.5 ml), and the mixture is stirred for 50 minutes. The reaction mixture is mixed with ethanol (2 ml) and stirred at the same temperature for 5 minutes and mixed with 1N-hydrochloric acid (5 ml) and water (200 ml) The aqueous layer is taken, washed with ethyl acetate, and concentrated under reduced pressure to remove remaining organic solvents. The resulting aqueous layer is subjected to chromatography over styrene- divinylbenzene copolymer (methanol : water=4:1). The eluting material is washed with ethyl acetate to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-propenyloxyimino)acetamido]-3-(1,2,3-triazol-4-ylthiomethylthio) -3-cephem-4-carboxylic acid (127 mg) as white solid. Yield : 50%.

Workup

  1. stirringstirred at the same temperature for 5 minutes
  2. washwashed with ethyl acetate
  3. concentrationconcentrated under reduced pressure
  4. customto remove
  5. washThe eluting material is washed with ethyl acetate

Sources & evidence

ORD record
ord-2952481d5fdd412dbd09709218263479
Source dataset
uspto-grants-1993_05
Patent number
US05214037

Reaction notes

Loading…