Trifluoroacetic acid → HCID 68766981, compound

HRID 989954Notes

Reaction equation

HRID 989954 reaction equation
[C:1]([O:5][C:6](=[O:28])[CH2:7][CH2:8][CH2:9][O:10][C:11](=[O:27])[C@H:12]([CH:24]([CH3:26])[CH3:25])[NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])(C)(C)C.FC(F)(F)C(O)=O.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:54]CI>O1CCOCC1>[Cl:54][CH2:1][O:5][C:6](=[O:28])[CH2:7][CH2:8][CH2:9][O:10][C:11](=[O:27])[C@H:12]([CH:24]([CH3:26])[CH3:25])[NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11644ChloroiodomethaneHCID 2723671Tetrabutylammonium HydroxideHCID 68766963HCID 68766963, compound

Product 1

HCID 68766981HCID 68766981, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-(N-CBz-L-valyloxy) butyric acid t-butyl ester (20 g, 50.8 mmole) was treated with trifluoroacetic acid (30 ml) at 0° C. for 3 h and then evaporated. The residue was coevaporated with toluene several time. The intermediate acid (2.56 g, 7.6 mmole) was dissolved in dioxane (10 ml) and to the solution was added tetrabutylammonium hydroxide (40%, 4.66 ml, 7.2 mmole). The solution was dried and dissolved in dichloromethane (20 ml) and then chloroiodomethane (10 ml, 144 mmole) was added to the solution. After 18 hr, the reaction solution was evaporated and the product was isolated with silica gel column chromatography. Yield 2.1 g.

Workup

  1. customevaporated
  2. customThe solution was dried
  3. dissolutiondissolved in dichloromethane (20 ml)
  4. customthe reaction solution was evaporated
  5. customthe product was isolated with silica gel column chromatography

Sources & evidence

ORD record
ord-82f2333c35cb4ea5a60486a68a3b3557
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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