Sodium Iodide → HCID 89495917, compound

HRID 1885269Notes

Reaction equation

HRID 1885269 reaction equation
[CH3:1][O:2][C:3]1[CH:43]=[CH:42][C:6]([CH2:7][O:8][C:9]([C:11]2[N:16]3[C:17](=[O:39])[C@@H:18](NC(=O)C(C4N=C(NC(OC(C)(C)C)=O)SC=4)=NOC)[C@H:15]3[S:14][CH2:13][C:12]=2[CH2:40]Cl)=[O:10])=[CH:5][CH:4]=1.[I-:44].[Na+]>CC(C)=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:43]=[CH:42][C:6]([CH2:7][O:8][C:9]([C:11]2[N:16]3[C:17](=[O:39])[CH2:18][C@H:15]3[S:14][CH2:13][C:12]=2[CH2:40][I:44])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 123160304HCID 123160304, compound

Product 1

HCID 89495917HCID 89495917, compoundYield 163.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7β-[2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-methoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (652 mg: 1 mMol.) in acetone (7 ml) is added sodium iodide (450 mg: 3 Eq.), and the mixture is stirred at room temperature for 1 hour. The reaction mixture is diluted with ethyl acetate, washed with water, dried, and concentrated under reduced pressure to give 7β-[2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-methoxyimino) acetamido]-3-iodomethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (730 mg). Yield: 98%.

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f41e76d8b94749509dbeb7f8cbc6d285
Source dataset
uspto-grants-1992_09
Patent number
US05143910

Reaction notes

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