Anisole → HCID 141560923, compound

HRID 1681166Notes

Reaction equation

HRID 1681166 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[NH2:5][C:6]1[S:7][CH:8]=[C:9](/[C:11](=[N:54]/[O:55][CH3:56])/[C:12]([NH:14][CH:15]2[C:52](=[O:53])[N:17]3[C:18]([C:36]([O:38]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:37])=[C:19]([C:22]4[C:25](=[O:26])[C:24](=[O:27])[C:23]=4[O:28]CC4C=CC=CC=4)[CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1.C1(OC)C=CC=CC=1>[N+](C)([O-])=O.C(Cl)Cl.Cl>[NH2:5][C:6]1[S:7][CH:8]=[C:9](/[C:11](=[N:54]/[O:55][CH3:56])/[C:12]([NH:14][CH:15]2[C:52](=[O:53])[N:17]3[C:18]([C:36]([OH:38])=[O:37])=[C:19]([C:22]4[C:23](=[O:28])[C:24](=[O:27])[C:25]=4[OH:26])[CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1

Participants

7

Reactant 3

HCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 141560925HCID 141560925, compound

Product 1

HCID 141560923HCID 141560923, compoundYield 7.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 6375NitromethaneSolvent

Procedure

A solution of aluminum chloride (82 mg, 0.612 mmol) in nitromethane (1 mL) was added rapidly to a stirred, cooled (ice/H2O bath) solution of diphenylmethyl 7-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-(2-benzyloxy-3,4-dioxo-1-cyclobutenyl)-3-cephem-4-carboxylate (50 mg, 0.068 mmol) and anisole (66 mg, 0.612 mmol) in CH2Cl2 (1 mL). The mixture was stirred with cooling for 0.33 hr and then for 2 hrs at ambient temperatures. The solution was cooled and diluted with dilute aqueous hydrochloric acid to precipitate a solid which was collected and discarded. The aqueous filtrate was washed with ethyl acetate. The aqueous layer was applied to a Michel-Miller HPLPLC column (22×130 mm) containing Partisil Prep 40 ODS-3. The column was eluted with a mixture of H2O-acetonitrile-acetic acid (90:10:0.5). The appropriate fractions were combined and the organic solvents removed. Lyophilization of the aqueous solution afforded the title compound (2.5 mg, 7.7 % yield) as a bright yellow solid.

Workup

  1. temperaturewith cooling for 0.33 hr
  2. temperatureThe solution was cooled
  3. customto precipitate a solid which
  4. customwas collected
  5. washThe aqueous filtrate was washed with ethyl acetate
  6. additioncontaining Partisil Prep 40 ODS-3
  7. washThe column was eluted with a mixture of H2O-acetonitrile-acetic acid (90:10:0.5)
  8. customthe organic solvents removed

Sources & evidence

ORD record
ord-88d799f719fa4f648507079a3fa6662d
Source dataset
uspto-grants-1992_12
Patent number
US05169843

Reaction notes

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