Sodium Iodide → HCID 131720388, compound

HRID 1740361Notes

Reaction equation

HRID 1740361 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:34](=[O:35])[N:13]3[C:14]([C:22]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)=[O:23])=[C:15]([CH:18]=[CH:19][CH2:20]Cl)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I-:36].[Na+]>CC(C)=O>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:34](=[O:35])[N:13]3[C:14]([C:22]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)=[O:23])=[C:15]([CH:18]=[CH:19][CH2:20][I:36])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 131720389HCID 131720389, compound

Product 1

HCID 131720388HCID 131720388, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

After 20.0 g of p-methoxybenzyl 7β-[2-phenylacetamido]-3-[3-chloro-1-propenyl]-3-cephem-4-carboxylate (E/Z=25/75) was suspended in 250 ml of acetone, 29 g of sodium iodide was added to the suspension. The mixture was reacted at 25-30° C. for 3 hours, while stirring. After the reaction was completed, the solution was concentrated at a temperature below 25° C. under a reduced pressure of 100 mmHg and 60 ml of acetone was distilled off. The formed crystals were collected by filtration and washed successively with 50 g of 5% sodium thiosulfate aqueous solution, next with 50 g of ion exchange water and finally with 50 g of acetone to give 14.24 g of p-methoxybenzyl 7β-[2-phenylacetamido]-3-[3-iodo-1-propenyl]-3-cephem-4-carboxylate (content, 97.0%; E/Z=99/1). The yield of E-form was 59%.

Workup

  1. customThe mixture was reacted at 25-30° C. for 3 hours
  2. concentrationthe solution was concentrated at a temperature below 25° C. under a reduced pressure of 100 mmHg and 60 ml of acetone
  3. distillationwas distilled off
  4. filtrationThe formed crystals were collected by filtration
  5. washwashed successively with 50 g of 5% sodium thiosulfate aqueous solution, next with 50 g of ion exchange water and finally with 50 g of acetone

Sources & evidence

ORD record
ord-3443d0c796154f9abe8b4b859e27cbe3
Source dataset
uspto-grants-1999_10
Patent number
US05969131

Reaction notes

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