Chloroiodomethane → HCID 54441965, compound

HRID 1790778Notes

Reaction equation

HRID 1790778 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([OH:24])=[O:23])=[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:46][CH2:47]I>O1CCOCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([O:24][CH2:47][Cl:46])=[O:23])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11644ChloroiodomethaneHCID 2723671Tetrabutylammonium HydroxideHCID 53966558HCID 53966558, compound

Product 1

HCID 54441965HCID 54441965, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-(N-benzyloxycarbonyl-valyloxy)benzoic acid (7.42 g, 20 mmole) in 1,4-dioxane (100 ml) was added a 40% solution of tetrabutylammonium hydroxide (12.97 g, 20 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 dichloromethane (50 ml) and chloroiodomethane (35.3 g, 200 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: 3.8 g=45%.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. dissolutionThe dried product was dissolved in dichloromethane (50 ml)
  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-127fc892cc714e3a87233a5a5f30f622
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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