Sodium Iodide → HCID 53848558, compound

HRID 249601Notes

Reaction equation

HRID 249601 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 (11.5 g: 30.0 mMol.) in acetone (150 ml) is added sodium iodide (9.00 g: 60.0 mMol.), and the mixture is stirred t 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 sodiumsulfate, 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%. NMR δ (CDCl3) ppm: 1.49(s, 9H), 3.19, 3.82(ABq, J=18.5Hz, 2H), 4.19(d, J=4.6Hz, 1H), 4.16, 4.22(ABq, J=13.7Hz, 2H), 6.19(dd, J=4.6Hz, J=10.1Hz, 1H), 6.97(s, 1H), 7.05-7.5(m, 41H), 7.90(s, 1H), 8.04(d, J=10.1Hz, 1H), 8.30(brs, 1H). IR ν (CHCl3) cm-1 : 3400, 1804, 1725, 1689, 1543, 1496, 1449, 1371, 1040. 2) Acyl=(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetyl: Het=1-methyl-1.2.4-triazol-3-yl (4E3-2)

Workup

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

Sources & evidence

ORD record
ord-b8355fa103c44fb6b5dab7fefaddd4ca
Source dataset
uspto-grants-1993_05
Patent number
US05214037

Reaction notes

Loading…