Sodium Iodide → HCID 131716307, compound

HRID 1198923Notes

Reaction equation

HRID 1198923 reaction equation
Cl[CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[CH:22]([NH:23][C:24](=[O:71])[CH:25]([C:46]3[N:47]=[C:48]([NH:51][C:52]([C:65]4[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=4)([C:59]4[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=4)[C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)[S:49][CH:50]=3)[O:26][CH:27]([C:30]([O:32][CH:33]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:31])[CH2:28][F:29])[C:21](=[O:72])[N:7]2[C:8]=1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)=[O:10].[I-:73].[Na+]>CC(C)=O>[I:73][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[CH:22]([NH:23][C:24](=[O:71])[CH:25]([C:46]3[N:47]=[C:48]([NH:51][C:52]([C:65]4[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=4)([C:59]4[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=4)[C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)[S:49][CH:50]=3)[O:26][CH:27]([C:30]([O:32][CH:33]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:31])[CH2:28][F:29])[C:21](=[O:72])[N:7]2[C:8]=1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)=[O:10]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 131716308HCID 131716308, compound

Product 1

HCID 131716307HCID 131716307, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

130 mg (0.125 mmol) of p-methoxybenzyl 3-chloromethyl-7-{2-(2-tritylamino-4-thiazolyl)-2-(1-diphenylmethoxycarbonyl-2-fluoroethoxy) acetamido}-ceph-3-em-4-carboxylate-syn isomer was dissolved in 1 l ml of acetone, and 0.5 ml of acetone solution containing 28 mg (0.19 mmol) of sodium iodide was added to the resulting solution at room temperature and reacted for 40 minutes. After the reaction, the solvent was distilled out, methylene chloride was added to the resulting residue, the insoluble materials were filtrated out, and the remaining filtrate was concentrated under reduced pressure to obtain p-methoxybenzyl 3-iodomethyl-7-{2-(2-tritylamino-4-thiazolyl)-2-(1-diphenylmethoxycarbonyl-2-fluoroethoxy)acetamido}-ceph-3-em-4-carboxylate-syn isomer. To this was added 23 mg (0.15 mmol) of 1-(2-fluoroethyl)-4-pyridothione, and the resulting mixture was dissolved in 1 ml of chloroform and reacted for 1 hour at room temperature. After the reaction, the chloroform was distilled out under reduced pressure, and the residue was purified by silicagel-chromatography (chloroform/methanol=10/1) and dissolved in 0.15 ml of anisole, and then, 1.5 ml of trifluoroacetic acid was added thereto, while cooled with ice, and reacted for 1 hour. After the reaction, isopropylether was added to the reaction solution to form a precipitate therein. After dried, 70 mg of a powder was obtained. To this was added 1 ml of water and the pH value of the resulting solution was adjusted to 7.8 with sodium hydrogencarbonate, and the solution was purified with HP-b 20 resin (methanol/H2O=1/4) to obtain 32 mg of the above entitled compound.

Workup

  1. additionwas added to the resulting solution at room temperature
  2. customreacted for 40 minutes
  3. customAfter the reaction
  4. distillationthe solvent was distilled out
  5. additionmethylene chloride was added to the resulting residue
  6. filtrationthe insoluble materials were filtrated out
  7. concentrationthe remaining filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6b5ba8bc34a7441fb0d5e85177fe0c67
Source dataset
uspto-grants-1990_02
Patent number
US04898858

Reaction notes

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