Benzyl Bromide → 3-(1-benzyl-1H-imidazol-4-yl)-2-tert-butoxycarbonylamino-propionic acid benzyl ester

HRID 852856Notes

Reaction equation

HRID 852856 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[N:15]=[CH:16][NH:17][CH:18]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:19]([O:11][C:10](=[O:12])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][C:14]1[N:15]=[CH:16][N:17]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178453337HCID 178453337, compound

Product 1

HCID 694161093-(1-benzyl-1H-imidazol-4-yl)-2-tert-butoxycarbonylamino-propionic acid benzyl esterYield 30,273.199%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-tert-Butoxycarbonylamino-3-(1H-imidazol-4-yl)-propionic acid (25 g, 97.92 mmol), benzyl bromide (17.59 g, 12.2 mL, 0.103 mmol) and potassium carbonate (16.9 g, 0.122 mol) in DMF (250 mL) were stirred overnight under argon. The solvent was removed and the residue taken up into water and CH2Cl2. The organic layer was washed with water and brine, dried and filtered. The solvent was removed and the residue subject to column chromatography (silica gel, 75% EA/PE to afford 3-(1-benzyl-1H-imidazol-4-yl)-2-tert-butoxycarbonylamino-propionic acid benzyl ester (6.79 g, 16%) Rf 0.6, followed by 10% MeOH/EA to afford the title compound (15.832 g, 47%) Rf 0.1). ESMS 346 (M+H+) Mpt 100.5-101.7° C. 1H NMR (500 MHz, CDCl3) δ 1.42 (9H, s), 3.02 (2H, m), 4.51 (1H, m), 5.19 (1H, d, J=12.1 Hz), 5.08 (1H, d, J=12.1 Hz), 5.81 (1H, m), 7.35 (5H, m), 7.47 (1H, s). 13C NMR (CDCl3) δ 28.22, 29.48, 53.67, 66.88, 79.88, 116.23, 126.63, 128.26, 128.45, 133.61, 135.19, 135.39, 155.59, 171.97.

Workup

  1. customThe solvent was removed
  2. washThe organic layer was washed with water and brine
  3. customdried
  4. filtrationfiltered
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-285353060f944e09ab27dd5e632792c0
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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