Sodium Iodide → HCID 13180425, compound

HRID 653558Notes

Reaction equation

HRID 653558 reaction equation
[C:1]([O:5][C:6]([C:8]([CH3:69])([O:10]/[N:11]=[C:12](/[C:44]1[N:45]=[C:46]([NH:49][C:50]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[S:47][CH:48]=1)\[C:13]([NH:15][CH:16]1[C:42](=[O:43])[N:18]2[C:19]([C:26]([O:28][CH:29]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])=[C:20]([CH2:24]Cl)[CH2:21][S:22](=[O:23])[C@H:17]12)=[O:14])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[I-:70].[Na+].C(OCC)(=O)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>CC(C)=O>[C:1]([O:5][C:6]([C:8]([CH3:69])([O:10]/[N:11]=[C:12](/[C:44]1[N:45]=[C:46]([NH:49][C:50]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[S:47][CH:48]=1)\[C:13]([NH:15][CH:16]1[C:42](=[O:43])[N:18]2[C:19]([C:26]([O:28][CH:29]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])=[C:20]([CH2:24][I:70])[CH2:21][S:22](=[O:23])[C@H:17]12)=[O:14])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 24477Sodium ThiosulfateHCID 13180419HCID 13180419, compound

Product 1

HCID 13180425HCID 13180425, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The compound obtained in (A) was dissolved in 200 ml of acetone, and 3.38 g (22.5 mmol) of sodium iodide was added. The mixture was stirred at room temperature for 30 minutes. To the reaction solution, 600 ml of ethyl acetate and 200 ml of a 10% sodium thiosulfate aqueous solution were added for extraction. Then, the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by slica gel flush column chromatography (ethyl acetate/n-hexane=1/2), and concentrated under reduced pressure. Then, diisopropyl ether was added thereto, and 7.0 g (yield: 63.0%) of a powder of the above-identified compound was collected by filtration.

Workup

  1. dry with materialThen, the organic layer was dried over anhydrous sodium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by slica gel
  4. customflush column chromatography (ethyl acetate/n-hexane=1/2)
  5. concentrationconcentrated under reduced pressure
  6. additionThen, diisopropyl ether was added

Sources & evidence

ORD record
ord-1e9d821588904a88a048416c4775e972
Source dataset
uspto-grants-1987_06
Patent number
US04677100

Reaction notes

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