Sodium hydride → 3-(4-Bromo-phenyl)-6-tert-butoxycarbonylamino-hexanoic acid ethyl ester

HRID 1784704Notes

Reaction equation

HRID 1784704 reaction equation
C(O[C:4](=O)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)C.[H-].[Na+].[C:16]([O:20][C:21](=[O:27])[NH:22][CH2:23][CH2:24][CH2:25]Br)([CH3:19])([CH3:18])[CH3:17]>CS(C)=O>[CH2:16]([O:20][C:21](=[O:27])[CH2:4][CH:5]([C:6]1[CH:7]=[CH:8][C:9]([Br:12])=[CH:10][CH:11]=1)[CH2:25][CH2:24][CH2:23][NH:22][C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:27])[CH3:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 7020609Ethyl 2-(4-bromophenyl)acetate

Product 1

HCID 671174423-(4-Bromo-phenyl)-6-tert-butoxycarbonylamino-hexanoic acid ethyl esterYield 137.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of (4-bromo-phenyl)-acetic acid ethyl ester (2.31 g, 9.50 mmol) in dimethylsulfoxide (6 mL) was added to the suspension of sodium hydride (407 mg, 60% in oil, 10.17 mmol) and stirred 3 min. A solution of (3-bromo-propyl)-carbamic acid tert-butyl ester (2.03 g, 8.52 mmol) in dimethylsulfoxide (6 mL) was added to the solution and stirred at 50° C. for 30 min. The resulting solution was partitioned between ethyl acetate and saturated aqueous ammonium chloride. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and brine, dried by passing through Celite column, and concentrated in vacuo. The residue was purified by silica gel chromatography eluting ethyl acetate/hexane (4/1 to 3/1, v/v) to afford 3-(4-Bromo-phenyl)-6-tert-butoxycarbonylamino-hexanoic acid ethyl ester (2.43 g, 74%).

Workup

  1. stirringstirred at 50° C. for 30 min
  2. customThe resulting solution was partitioned between ethyl acetate and saturated aqueous ammonium chloride
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer was washed with water and brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluting ethyl acetate/hexane (4/1 to 3/1

Sources & evidence

ORD record
ord-5cb2562ed8414c3ebd14754b80b80c00
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

Loading…