1-Hydroxybenzotriazole → Boc-Val-Pro-OBzl

HRID 487736Notes

Reaction equation

HRID 487736 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([OH:15])=O)[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:17]([O:24][C:25](=[O:31])[C@@H:26]1[CH2:30][CH2:29][CH2:28][NH:27]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH2:17]([O:24][C:25](=[O:31])[C@@H:26]1[CH2:30][CH2:29][CH2:28][N:27]1[C:13](=[O:15])[C@H:9]([CH:10]([CH3:11])[CH3:12])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 83693Boc-L-ValineHCID 2733413Proline benzyl ester hydrochloride

Product 1

HCID 14304307Boc-Val-Pro-OBzlYield 99.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(tert-butoxycarbonyl)-L-valine (10.86 g) and L-proline benzyl ester hydrochloride (12.09 g) in DMF (50 ml) were added HOBT (6.76 g) and WSCD (7.76 g) under ice-bath cooling. After being stirred at room temperature for 18 hours, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (400 ml) and washed with 5% aqueous citric acid (200 ml) saturated aqueous sodium bicarbonate (200 ml). The solution was dried over magnesium sulfate and evaporated under reduced pressure to give N-(tert-butoxycarbonyl)-L-valyl-L-proline benzyl ester (20.06 g) as an oil.

Workup

  1. temperaturecooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (400 ml)
  4. washwashed with 5% aqueous citric acid (200 ml) saturated aqueous sodium bicarbonate (200 ml)
  5. dry with materialThe solution was dried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-84cfb286de4f4ef593bcbeb7db5a7fb0
Source dataset
uspto-grants-1994_03
Patent number
US05296591

Reaction notes

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