Chloroiodomethane → HCID 53675844, compound

HRID 489027Notes

Reaction equation

HRID 489027 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:42][CH2:43]I>O1CCOCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH2:20][C:21]([O:23][CH2:43][Cl:42])=[O:22])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11644ChloroiodomethaneHCID 2723671Tetrabutylammonium HydroxideHCID 23387363HCID 23387363, compound

Product 1

HCID 53675844HCID 53675844, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-(N-benzyloxycarbonyl-L-valyloxy)propanoic acid (5.2 g, 16.08 mmole) in 1,4-dioxane (50 ml) was added a 40% solution of tetrabutylammonium hydroxide (10.43 g, 16.08 mmole) and the mixture was stirred 2 hours at room temperature. The mixture was evaporated under reduced pressure and co-evaporated two times with 1,4-dioxane and two times with toluene. The dried product was dissolved in 40 ml dichloromethane and chloroiodomethane (28.4 g. 160 mmole) was added. The solution was stirred for two days at room temperature and evaporated under reduced pressure. Ethyl acetate (100 ml) was added and the organic phase washed twice with water, dried with sodium sulfate and evaporated under reduced pressure. The product was isolated by silica gel column chromatography. Yield: 2.2 g=35%

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. dissolutionThe dried product was dissolved in 40 ml dichloromethane
  3. stirringThe solution was stirred for two days at room temperature
  4. customevaporated under reduced pressure
  5. additionEthyl acetate (100 ml) was added
  6. washthe organic phase washed twice with water
  7. dry with materialdried with sodium sulfate
  8. customevaporated under reduced pressure
  9. customThe product was isolated by silica gel column chromatography

Sources & evidence

ORD record
ord-06fca9b190144e2483ce4fa4f815a23c
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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