Chloroiodomethane → HCID 54147622, compound

HRID 1170568Notes

Reaction equation

HRID 1170568 reaction equation
[CH3:1][C:2]([CH3:22])([CH2:6][O:7][C:8](=[O:21])[C@H:9]([CH:18]([CH3:20])[CH3:19])[NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:3]([OH:5])=[O:4].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:41][CH2:42]I>O1CCOCC1>[Cl:41][CH2:42][O:4][C:3](=[O:5])[C:2]([CH3:1])([CH3:22])[CH2:6][O:7][C:8](=[O:21])[C@H:9]([CH:18]([CH3:19])[CH3:20])[NH:10][C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12]

Participants

5

Reactant 3

HCID 11644ChloroiodomethaneHCID 2723671Tetrabutylammonium HydroxideHCID 23387338HCID 23387338, compound

Product 1

HCID 54147622HCID 54147622, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,2-dimethyl-3-(N-Boc-L-valyloxy)propionic acid (3.9 g, 12.3 mmole) was dissolved in dioxane (60 ml). To the solution was added tetrabutylammonium hydroxide aqueous solution (40%, 7.78 ml, 12 mmole). The solution was dried in vacuo, and it was coevaporated with toluene for several times. The residue was dissolved in methylene chloride and then chloroiodomethane (18.9 ml, 260 mmole) was added to the solution. After 18 hr, the reaction solution was evaporated and the product was isolated with silica gel column chromatography to yield 3.7 g.

Workup

  1. customThe solution was dried in vacuo, and it
  2. dissolutionThe residue was dissolved in methylene chloride
  3. customthe reaction solution was evaporated
  4. customthe product was isolated with silica gel column chromatography
  5. customto yield 3.7 g

Sources & evidence

ORD record
ord-aea3a55cf32e48f3b8ff0d50d0d424d4
Source dataset
uspto-grants-2010_11
Patent number
US07825238B2

Reaction notes

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