Ethanol → HCID 10075720, compound

HRID 1707490Notes

Reaction equation

HRID 1707490 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:68][CH:69]=[N:70][N:71]=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:68][CH:69]=[N:70][N:71]=4)[CH2:19][S:20][C@H:21]23)=[O:62])[N:50]=1

Participants

8

Reactant 3

HCID 702EthanolHCID 6451240Aluminum(III) ChlorideHCID 9988646HCID 9988646, compound

Product 1

HCID 10075720HCID 10075720, compoundYield 74.1%

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-(1,3,4-thiadiazol-2-ylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester (535 mg: 0.51 mMol.) in a mixture of anisole (1 ml) and nitromethane (4 ml) is added a solution of aluminum chloride (0.61 g: 4.6 mMol.) in anisole (2 ml) at -30° C. 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, diluted with 1N-hydrochloric acid (6 ml) and water (200 ml), and washed with ethyl acetate. The aqueous layer is concentrated under reduced pressure to remove the organic solvents and passed through a styrene-divinylbenzene copolymer column. The adsorbed material is eluted with a methanol-water (4:1) mixture. The eluate is concentrated to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-(1,3,4-thiadiazol-2-ylthiomethylthio)-3-cephem-4-carboxylic acid as pale yellow solid (201 mg). Yield: 74%.

Workup

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

Sources & evidence

ORD record
ord-62d357fa466f4257a64596a1c8e989c9
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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