Benzyl Bromide → N-t-Butoxycarbonyl Statine benzyl ester

HRID 579901Notes

Reaction equation

HRID 579901 reaction equation
[C:1]([O:5][C:6]([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:7])([CH3:4])([CH3:3])[CH3:2].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:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[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 esterYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(t-butyloxycarbonyl)-statine (1141 mg., 5.12 mmol) were dissolved in 20 ml of dimethylformamide. 708 mg. of potassium carbonate and 0.609 ml of benzyl bromide was then added. After the reaction was complete, the reaction mixture was concentrated, taken up in ethyl acetate, washed twice with 5 ml of H2O, dried over MgSO4, filtered and concentrated to yield 1510 mg of a yellow oil (81% yield). 1H NMR, 90 mHz, CDCl3, partial, 0.92 (d, J=7 Hz, 6H), 1.42 (s, 9H, Boc), 2.58 (m, 2H), 4.05 (m, 1H), 4.72 (d, BocNH, 1H), 5.13 (s, CH20, 2H), 7.3 (s, 5H, aromatic).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. washwashed twice with 5 ml of H2O
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-903003ddab4943b7a876e834f82a738b
Source dataset
uspto-grants-1988_06
Patent number
US04749687

Reaction notes

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