Ethanol → HCID 10415042, compound

HRID 1707491Notes

Reaction equation

HRID 1707491 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][CH2:65][S:66][C:67]2[S:71][C:70]([CH3:72])=[N:69][N:68]=2)=[O:16])C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].C(O)C>C1(OC)C=CC=CC=1.[N+](C)([O-])=O.Cl.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:66][C:67]4[S:71][C:70]([CH3:72])=[N:69][N:68]=4)[CH2:19][S:20][C@H:21]23)=[O:62])[N:50]=1

Participants

8

Reactant 3

HCID 702EthanolHCID 6451240Aluminum(III) ChlorideHCID 10034067HCID 10034067, compound

Product 1

HCID 10415042HCID 10415042, compoundYield 75%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6375NitromethaneSolventHCID 7519AnisoleSolvent2×

Procedure

To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-(2-methyl-1,3,4-thiadiazol-5-ylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester (388 mg: 0.368 mMol.) in a mixture of anisole (1 ml) and nitromethane (4 ml) at -30° C. is added a solution of aluminum chloride (0.45 g: 9.2 equivalents: 3.4 mMol.) in anisole (1.5 ml), and the mixture is stirred for 40 minutes. The reaction mixture is mixed with ethanol (2 ml), stirred for 5 minutes at the same temperature, and diluted with 1N-hydrochloric acid (6 ml) and water (200 ml). The aqueous layer is taken, washed with ethyl acetate, concentrated under reduced pressure to remove the organic solvents, and passed through a column of styrene-divinylbenzene copolymer. The column is eluted with methanol-water(4:1). The eluate is concentrated to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-(2-methyl-1,3,4-thiadiazol-5-ylthiomethylthio)-3 -cephem-4-carboxylic acid (149 mg). Yield: 75%.

Workup

  1. stirringstirred for 5 minutes at the same temperature
  2. washwashed with ethyl acetate
  3. concentrationconcentrated under reduced pressure
  4. customto remove the organic solvents
  5. washThe column is eluted with methanol-water(4:1)
  6. concentrationThe eluate is concentrated

Sources & evidence

ORD record
ord-99ae9a25f15b432b9fb3ea83df982ff9
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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