Boc-L-Valine → HCID 57433140, compound

HRID 1790753Notes

Reaction equation

HRID 1790753 reaction equation
[C:1]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:34]([O:41][C:42](=[O:47])[CH2:43][CH2:44][CH2:45]Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(=O)(O)[O-].[Na+]>O1CCOCC1>[CH2:34]([O:41][C:42](=[O:47])[CH2:43][CH2:44][CH2:45][O:14][C:13](=[O:15])[C@H:9]([CH:10]([CH3:11])[CH3:12])[NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 83693Boc-L-ValineHCID 516892Sodium BicarbonateHCID 2723671Tetrabutylammonium HydroxideHCID 3832489Benzyl 4-bromobutanoate

Product 1

HCID 57433140HCID 57433140, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-Boc-L-valine (1.3 g, 6 mmole) was dissolved in dioxane (5 ml). To the solution was added tetrabutylammonium hydroxide aqueous solution (40%, 3.8 ml, 6 mmole), and the solution was evaporated and coevaporated with toluene several times. The residue was dissolved in DMF (15 ml) and 4-bromobutyric acid benzyl ester (1.28 g, 5 mmole) was added to it. The reaction was kept for 18 hr, and then poured into sodium bicarbonate aqueous solution and extracted with dichloromethane. The organic phase was dried and the product was isolated with silica gel column chromatography, 1.2 g.

Workup

  1. customthe solution was evaporated
  2. dissolutionThe residue was dissolved in DMF (15 ml)
  3. extractionextracted with dichloromethane
  4. customThe organic phase was dried
  5. customthe product was isolated with silica gel column chromatography, 1.2 g

Sources & evidence

ORD record
ord-22938041f184471290a132a36fbb3439
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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