Sodium Iodide → HCID 141551542, compound

HRID 653560Notes

Reaction equation

HRID 653560 reaction equation
[CH:1]([O:14][C:15]([CH2:17][O:18]/[N:19]=[C:20](/[C:52]1[N:53]=[C:54]([NH:57][C:58]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)([C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[S:55][CH:56]=1)\[C:21]([NH:23][CH:24]1[C:50](=[O:51])[N:26]2[C:27]([C:34]([O:36][CH:37]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:35])=[C:28]([CH2:32]Cl)[CH2:29][S:30](=[O:31])[C@H:25]12)=[O:22])=[O:16])([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-:77].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+].C(OCC)(=O)C>CC(C)=O>[CH:1]([O:14][C:15]([CH2:17][O:18]/[N:19]=[C:20](/[C:52]1[N:53]=[C:54]([NH:57][C:58]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)([C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[S:55][CH:56]=1)\[C:21]([NH:23][CH:24]1[C:50](=[O:51])[N:26]2[C:27]([C:34]([O:36][CH:37]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:35])=[C:28]([CH2:32][I:77])[CH2:29][S:30](=[O:31])[C@H:25]12)=[O:22])=[O:16])([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

6

Reactant 4

HCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 24477Sodium ThiosulfateHCID 141551044HCID 141551044, compound

Product 1

HCID 141551542HCID 141551542, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The compound obtained in (A) was dissoved in 380 ml of acetone, and 7.4 g (49 mmol) of sodium iodide was added thereto. The mixture was stirred at room temperature for 30 minutes. To the reaction solution, 300 ml of a 10% sodium thiosulfate aqueous solution and 1150 ml of ethyl acetate were added for extraction. Then, the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel flush column chromatography (ethyl acetate/n-hexane =1/1) to obtain 22.4 g of a powder of the above-identified compound (yield from the previous step: 86.7%).

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 silica gel
  4. customflush column chromatography (ethyl acetate/n-hexane =1/1)

Sources & evidence

ORD record
ord-00a412ff7cc64548a2aea2cf6077eaf7
Source dataset
uspto-grants-1987_06
Patent number
US04677100

Reaction notes

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