Benzyl Bromide → N-t-Butoxycarbonyl Statine benzyl ester

HRID 745468Notes

Reaction equation

HRID 745468 reaction equation
[C:1]([NH:8][C@H:9]([C@H:14]([CH2:16][C:17](=[O:19])[OH:18])[OH:15])[CH2:10][CH:11]([CH3:13])[CH3:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C)C=O>[CH2:26]([O:19][C:17](=[O:18])[CH2:16][C@H:14]([OH:15])[C@H:9]([CH2:10][CH:11]([CH3:13])[CH3:12])[NH:8][C:1]([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2755962(3S,4S)-4-((tert-Butoxycarbonyl)amino)-3-hydroxy-6-methylheptanoic acid

Product 1

HCID 13961447N-t-Butoxycarbonyl Statine benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Boc-Statine, 8.83 g., was dissolved in dry dimethylformamide and treated at 25° C. for 4.5 hours with 4.43 g. potassium carbonate and 3.81 ml. benzyl bromide. The mixture was concentrated in vacuo, 500 ml. ethyl acetate was added and the suspension was washed with saturated aqueous lithium chloride (2×50 ml.), water (5×50 ml.), dried magnesium sulfate, filtered and concentrated to give 11.8 g. of a yellow syrup which was used without further purification.

Workup

  1. additiontreated at 25° C. for 4.5 hours with 4.43 g
  2. concentrationThe mixture was concentrated in vacuo, 500 ml
  3. additionethyl acetate was added
  4. washthe suspension was washed with saturated aqueous lithium chloride (2×50 ml.), water (5×50 ml.), dried magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give 11.8 g
  8. customof a yellow syrup which was used without further purification

Sources & evidence

ORD record
ord-b4a2aee01fc040aaab5114864d43b229
Source dataset
uspto-grants-1986_07
Patent number
US04599198

Reaction notes

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