Sodium Iodide → HCID 131726122, compound

HRID 724558Notes

Reaction equation

HRID 724558 reaction equation
C[O:2][C:3](=[O:63])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][C@@H:24]2[OH:27])[C@:20]2([CH3:21])[C@@H:15]([CH2:16][C@@H:17]([O:28][CH2:29][CH2:30][N:31]([C:33]4[CH:38]=[CH:37][C:36]([C@H:39]5[CH2:56][C@@:54]6([CH3:55])[C@@H:50]([CH2:51][CH2:52][C@:53]6([OH:60])[C:57]#[C:58][CH3:59])[C@H:49]6[C:40]5=[C:41]5[C:46]([CH2:47][CH2:48]6)=[CH:45][C:44](=[O:61])[CH2:43][CH2:42]5)=[CH:35][CH:34]=4)[CH3:32])[CH2:18][CH2:19]2)[CH2:14][C@H:13]3[OH:62])[CH2:10][CH2:9]1)[CH3:7].[C:64]([O:68][C:69]([NH:71][CH2:72][CH2:73][CH2:74][C:75]([O:77][CH2:78]Cl)=[O:76])=[O:70])([CH3:67])([CH3:66])[CH3:65].[CH:80](N(C(C)C)CC)(C)C.[Na+].[I-]>C(#N)C>[CH3:80][CH:4]([CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][C@@H:24]2[OH:27])[C@:20]2([CH3:21])[C@@H:15]([CH2:16][C@@H:17]([O:28][CH2:29][CH2:30][N:31]([C:33]4[CH:38]=[CH:37][C:36]([C@H:39]5[CH2:56][C@@:54]6([CH3:55])[C@@H:50]([CH2:51][CH2:52][C@:53]6([OH:60])[C:57]#[C:58][CH3:59])[C@H:49]6[C:40]5=[C:41]5[C:46]([CH2:47][CH2:48]6)=[CH:45][C:44](=[O:61])[CH2:43][CH2:42]5)=[CH:35][CH:34]=4)[CH3:32])[CH2:18][CH2:19]2)[CH2:14][C@H:13]3[O:62][CH2:78][O:77][C:75](=[O:76])[CH2:74][CH2:73][CH2:72][NH:71][C:69]([O:68][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:70])[CH2:10][CH2:9]1)[CH3:7])[C:3]([OH:2])=[O:63]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 58743831HCID 58743831, compoundHCID 131726114HCID 131726114, compound

Product 1

HCID 131726122HCID 131726122, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound of Example 1I (1 mmol) is combined with an equimolar amount of the compound of Example 11A in 1 mL of acetonitrile. Diisopropylethylamine (2 eq) and NaI (20 mg) are added, and the resultant mixture is heated at 90 C for 20 hrs. The reaction mixture is partitioned between ethyl acetate and water; the organic extract is washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude material is purified on silica gel using a gradient of ethyl acetate in hexanes to provide the title compound.

Workup

  1. customThe reaction mixture is partitioned between ethyl acetate and water
  2. extractionthe organic extract
  3. washis washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material is purified on silica gel using a gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-0ed900d357ee440396269f131b56728a
Source dataset
uspto-grants-2006_11
Patent number
US07141559B2

Reaction notes

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