Chloroiodomethane → HCID 23387568, compound

HRID 489039Notes

Reaction equation

HRID 489039 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)=[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.I[CH2:49][Cl:50]>O1CCOCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([O:27][CH2:49][Cl:50])=[O:26])=[CH:23][CH:22]=1)=[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 23387535HCID 23387535, compound

Product 1

HCID 23387568HCID 23387568, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-(2-N-benzyloxycarbonyl-L-valyloxyethyl)benzoic acid (2.0 g, 5.0 mmole) in 1,4-dioxane (20 ml) was added a 40% solution of tetrabutylammonium hydroxide (3.1 g, 4.75 mmole) and the mixture was stirred 2 hours at room temperature. The mixture was evaporated under reduced pressure and coevaporated two times with 1,4-dioxane and two times with toluene. The dried product was dissolved in dichloromethane (10 ml) and iodochloromethane (13.2 g, 75 mmole) was added. The solution was stirred overnight at room temperature and evaporated under reduced pressure. About 50 ml ethyl acetate were 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: 0.5 g=23%

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. dissolutionThe dried product was dissolved in dichloromethane (10 ml)
  3. stirringThe solution was stirred overnight at room temperature
  4. customevaporated under reduced pressure
  5. additionAbout 50 ml ethyl acetate were 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-a867197024374d0da2f462856eaf24e9
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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