Sodium Iodide → 1-[(2S)-3-(4-iodobutoxycarbonyl) mercapto-2-methyl-1-oxopropyl]-L-proline

HRID 1375693Notes

Reaction equation

HRID 1375693 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]([S:9][CH2:10][C@@H:11]([CH3:22])[C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17])=[O:13])=[O:8].[Na+].[I-:24]>CC#N>[I:24][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]([S:9][CH2:10][C@@H:11]([CH3:22])[C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17])=[O:13])=[O:8]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 865955001-[(2S)-3-(4-chlorobutoxycarbonyl)mercapto-2-methyl-1-oxopropyl]-L-proline

Product 1

HCID 865955011-[(2S)-3-(4-iodobutoxycarbonyl) mercapto-2-methyl-1-oxopropyl]-L-prolineYield 102%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-[(2S)-3-(4-chlorobutoxycarbonyl)mercapto-2-methyl-1-oxopropyl]-L-proline (5.80 g, 0.0157 Mol) was dissolved in CH3CN (100 ml) and NaI (23.9 g, 0.160 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-[(2S)-3-(4-iodobutoxycarbonyl) mercapto-2-methyl-1-oxopropyl]-L-proline (7.10 g) as an oil 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-7146796ff2eb4267a7d74c7417a7db5c
Source dataset
uspto-grants-2007_01
Patent number
US07169805B2

Reaction notes

Loading…