Sodium Iodide → HCID 53848558, compound

HRID 1707448Notes

Reaction equation

HRID 1707448 reaction equation
[C:1]([C:20]1[NH:24][N:23]=[C:22]([S:25][CH2:26]Cl)[N:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:28].[Na+]>CC(C)=O.O>[C:1]([C:20]1[NH:24][N:23]=[C:22]([S:25][CH2:26][I:28])[N:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 54029991HCID 54029991, compound

Product 1

HCID 53848558HCID 53848558, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of trityl-3-chloromethylthio-1,2,4-triazole (11.75 g: 30.0 mMol.) in acetone (150 ml) is added sodium iodide (9.00 g: 60.0 mMol.), and the mixture is stirred at 50° C. for 3 hours. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is washed with brine, dried over sodium sulfate, and concentrated to give trityl-3-iodomethylthio-1,2,4-triazole as yellow crystals [NMR δ(CDCl3) ppm: 4.70(s, 2H), 7.1 to 7.2(m, 6H), 7.3 to 7.4(m, 9H), 7.96(s, 1H): 13 g]. To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetylamino]-3-argentiothio-3-cephem-4-carboxylic acid diphenylmethyl ester 1-oxide (16.8 g: 15 mMol.) in hexamethylphosphoramide (90 ml) is added trityl-3-iodomethylthio-1,2,4-triazole (13 g), and the mixture is stirred at room temperature for 3 hours. The reaction mixture is diluted with ethyl acetate, mixed with saturated brine, and filtered through Celite. The organic layer is taken, washed with brine, dried over sodium sulfate, and concentrated. The residue is purified by silica gel chromatography (toluene: ethyl acetate=5:1-3:1) to give 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetylamino]-3-(trityl-1,2,4-triazol-3-ylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester 1-oxide (11.29 g) as pale brown foam. Yield: 59%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cb3b269267f4445b94b080bd9ef74bfc
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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