Sodium Iodide → HCID 141558886, compound

HRID 1252315Notes

Reaction equation

HRID 1252315 reaction equation
[CH:1]([O:14][C:15]([C:17]1([O:22]/[N:23]=[C:24](/[C:56]2[N:57]=[C:58]([NH:61][C:62]([C:75]3[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=3)([C:69]3[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=3)[C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)[S:59][CH:60]=2)\[C:25]([NH:27][CH:28]2[C:54](=[O:55])[N:30]3[C:31]([C:38]([O:40][CH:41]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)=[O:39])=[C:32]([CH2:36]Cl)[CH2:33][S:34](=[O:35])[C@H:29]23)=[O:26])[CH2:21][CH2:20][CH2:19][CH2:18]1)=[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-:81].[Na+].C(OCC)(=O)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>CC(C)=O>[CH:1]([O:14][C:15]([C:17]1([O:22]/[N:23]=[C:24](/[C:56]2[N:57]=[C:58]([NH:61][C:62]([C:75]3[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=3)([C:69]3[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=3)[C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)[S:59][CH:60]=2)\[C:25]([NH:27][CH:28]2[C:54](=[O:55])[N:30]3[C:31]([C:38]([O:40][CH:41]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)=[O:39])=[C:32]([CH2:36][I:81])[CH2:33][S:34](=[O:35])[C@H:29]23)=[O:26])[CH2:21][CH2:20][CH2:19][CH2:18]1)=[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 141551043HCID 141551043, compound

Product 1

HCID 141558886HCID 141558886, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The residue obtained in (B) was dissolved in 40 ml of acetone, and 990 mg (6.6 mmol) of sodium iodide was added. The mixture was stirred at room temperature for 30 minutes. Then, 120 ml of ethyl acetate and 20 ml of a 5% sodium thiosulfate aqueous solution were added to the reaction solution for liquid separation. The organic layer was washed with water and with a saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate and concentrated. The concentrated residue was subjected to silica gel flush column chromatography (ethyl acetate/n-hexane=1/2). The fraction containing the desired product was collected, and concentrated under reduced pressure, and isopropyl ether was added to the residue to obtain 2.92 g of a powder of the above identified compound (yield from A: 80.3%).

Workup

  1. washThe organic layer was washed with water and with a saturated sodium chloride aqueous solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customflush column chromatography (ethyl acetate/n-hexane=1/2)
  5. additionThe fraction containing the desired product
  6. customwas collected
  7. concentrationconcentrated under reduced pressure, and isopropyl ether
  8. additionwas added to the residue

Sources & evidence

ORD record
ord-5217bbeae9c84116b6475631c9e1ecc5
Source dataset
uspto-grants-1988_05
Patent number
US04742053

Reaction notes

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