Chloroiodomethane → HCID 23387569, compound

HRID 1170633Notes

Reaction equation

HRID 1170633 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH:19]1[CH2:24][CH2:23][CH:22]([C:25]([OH:27])=[O:26])[CH2:21][CH2:20]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[CH2:47][Cl:48]>O1CCOCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH:19]1[CH2:24][CH2:23][CH:22]([C:25]([O:27][CH2:47][Cl:48])=[O:26])[CH2:21][CH2:20]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 23405699HCID 23405699, compound

Product 1

HCID 23387569HCID 23387569, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-(N-benzyloxycarbonyl-L-valyloxy) cyclohexanoic acid (6.6 g, 20 mmole) in 1,4-dioxane (70 ml) was added a 40% solution of tetrabutylammonium hydroxide (11.34 g, 17.5 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 60 ml dichloromethane and iodochloromethane (30.9 g, 175 mmole) was added. The solution was stirred for two days at room temperature and evaporated under reduced pressure. About 100 ml ethyl acetate 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 with toluene/acetone. Yield: 4.1 g=55%.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. dissolutionThe dried product was dissolved in 60 ml dichloromethane
  3. stirringThe solution was stirred for two days at room temperature
  4. customevaporated under reduced pressure
  5. additionAbout 100 ml ethyl acetate 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 with toluene/acetone

Sources & evidence

ORD record
ord-2b9cb4b42ed54e0cbcd34b0d4bdd5e27
Source dataset
uspto-grants-2010_11
Patent number
US07825238B2

Reaction notes

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