Dimethylformamide → Benzyl 6-(tert-butoxycarbonylamino)hexanoate

HRID 2205001Notes

Reaction equation

HRID 2205001 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CN(C=O)C>CC(C)=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium Carbonate2×HCID 6376026-((tert-Butoxycarbonyl)amino)hexanoic acid

Product 1

HCID 12160267Benzyl 6-(tert-butoxycarbonylamino)hexanoate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(tert-butoxycarbonylamino)hexanoic acid (1 eq) in acetone (0.2 M) was added potassium carbonate (2 eq) and (bromomethyl)benzene (2 eq) in acetone (2 M). The reaction mixture was stirred at room temperature for 1 hour. Additional amount of DMF was then added to the reaction mixture to facilitate the dissolution of potassium carbonate. The reaction mixture was stirred at room temperature for another 30 minutes. The mixture was then diluted with ethyl acetate, and washed with 5% citric acid, water and brine. The organic layer was dried over anhydrous Na2SO4, and concentrated en vaccuo. The crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 10-40% EtOAc/Hex to give the product.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for another 30 minutes
  2. washwashed with 5% citric acid, water and brine
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated en vaccuo
  5. customThe crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO)
  6. customto give the product

Sources & evidence

ORD record
ord-35a4fcc3c65944a18cada0ca48c8014d
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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