Sodium Iodide → HCID 131726114, compound

HRID 2112311Notes

Reaction equation

HRID 2112311 reaction equation
[OH:1][C@@H:2]1[CH2:26][C@H:25]2[C@:20]([CH3:41])([CH2:21][CH2:22][C@H:23]([O:27][CH2:28]COS(C3C=CC(C)=CC=3)(=O)=O)[CH2:24]2)[C@@H:19]2[C@@H:3]1[C@H:4]1[C@:16]([CH3:43])([C@@H:17]([OH:42])[CH2:18]2)[C@@H:7]([C@H:8]([CH3:15])[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH2:6][CH2:5]1.[OH:44][C@:45]1([C:72]#[C:73][CH3:74])[CH2:50][CH2:49][C@H:48]2[C@H:51]3[C:60]([C@@H:61]([C:63]4[CH:68]=[CH:67][C:66]([NH:69][CH3:70])=[CH:65][CH:64]=4)[CH2:62][C@:46]12[CH3:47])=[C:59]1[C:54](=[CH:55][C:56](=[O:71])[CH2:57][CH2:58]1)[CH2:53][CH2:52]3.[Na+].[I-].[CH:77](N(C(C)C)CC)(C)C>C(#N)C.CCCCCC.CCOC(C)=O>[OH:1][C@@H:2]1[CH2:26][C@H:25]2[C@:20]([CH3:41])([CH2:21][CH2:22][C@H:23]([O:27][CH2:28][CH2:70][N:69]([C:66]3[CH:65]=[CH:64][C:63]([C@H:61]4[CH2:62][C@@:46]5([CH3:47])[C@@H:48]([CH2:49][CH2:50][C@:45]5([OH:44])[C:72]#[C:73][CH3:74])[C@H:51]5[C:60]4=[C:59]4[C:54]([CH2:53][CH2:52]5)=[CH:55][C:56](=[O:71])[CH2:57][CH2:58]4)=[CH:68][CH:67]=3)[CH3:77])[CH2:24]2)[C@@H:19]2[C@@H:3]1[C@H:4]1[C@:16]([CH3:43])([C@@H:17]([OH:42])[CH2:18]2)[C@@H:7]([C@H:8]([CH3:15])[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH2:6][CH2:5]1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 13605510HCID 13605510, compoundHCID 58743810HCID 58743810, compound

Product 1

HCID 131726114HCID 131726114, compoundYield 69.5%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

The compound of Example 1C (15 g, 24.2 mmol) and the compound of Example 1H (11 g, 26.5 m mol), were combined with NaI (2.7 g), and diisopropylethylamine (3.12 g) in 400 mL of acetonitrile in a 1 liter pressure bottle. The solution was heated at 100° C. TLC (EtOAc:hexane, 60:40) or HPLC was checked for the completion of the reaction; no starting material was observed after 16 hours. The reaction mixture was cooled to ambient temperature and filtered through Celite; the solvents were removed in vacuo. The crude material was diluted with EtOAc (500 mL) and washed with saturated ammonium chloride solution (2×100 ml). The solvent was removed in vacuo, and the crude material was loaded on silica gel column to elute with hexane/EtOAc (3:2-1:1-2:3). Pure fractions were collected and concentrated to provide 14.5 g (63.3%) of the titled compound.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. filtrationfiltered through Celite
  3. customthe solvents were removed in vacuo
  4. additionThe crude material was diluted with EtOAc (500 mL)
  5. washwashed with saturated ammonium chloride solution (2×100 ml)
  6. customThe solvent was removed in vacuo
  7. washto elute with hexane/EtOAc (3:2-1:1-2:3)
  8. customPure fractions were collected
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-410d0ed4ef834e9fb72ed69d5ca03785
Source dataset
uspto-grants-2009_04
Patent number
US07521439B2

Reaction notes

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