Sodium Iodide → HCID 86595503, compound

HRID 1375695Notes

Reaction equation

HRID 1375695 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]([NH:9][C@H:10]([C:12]([CH:14]([SH:27])[C@@H:15]([CH3:26])[C:16]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([OH:22])=[O:21])=[O:17])=[O:13])[CH3:11])=[O:8].[Na+].[I-:29]>CC#N>[I:29][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]([NH:9][C@H:10]([C:12]([CH:14]([SH:27])[C@@H:15]([CH3:26])[C:16]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([OH:22])=[O:21])=[O:17])=[O:13])[CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 86595504HCID 86595504, compound

Product 1

HCID 86595503HCID 86595503, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-[(4-chlorobutoxycarbonyl)-L-alanyl-(2S)-3-mercapto-2-methyl-1-oxopropyl]-L-proline (3.15 g, 0.0078 Mol) was dissolved in CH3CN (100 ml) and NaI (11.7 g, 0.078 Mol) was added to the solution. The mixture was refluxed for 7 h, then concentrated and diluted with CH2Cl2. The solid formed was filtered off and the organic phase was washed with H2O (3×50 ml), dried over sodium sulphate and evaporated under reduced pressure affording 1-[(4-iodobutoxycarbonyl)-L-alanyl-(2S)-3-mercapto-2-methyl-1-oxopropyl]-L-proline (4.03 g) as a foam that was used without further purification.

Workup

  1. temperatureThe mixture was refluxed for 7 h
  2. concentrationconcentrated
  3. additiondiluted with CH2Cl2
  4. customThe solid formed
  5. filtrationwas filtered off
  6. washthe organic phase was washed with H2O (3×50 ml)
  7. dry with materialdried over sodium sulphate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e79ca7daca2e49f49dd86dbc5906e713
Source dataset
uspto-grants-2007_01
Patent number
US07169805B2

Reaction notes

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