Potassium Carbonate → 4-{[(2S)-2-Hydroxypropyl]amino}butyric acid tert.-butyl ester

HRID 1926910Notes

Reaction equation

HRID 1926910 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12](=[O:17])[CH2:13][CH2:14][CH2:15]Br)([CH3:10])([CH3:9])[CH3:8].[NH2:18][CH2:19][C@@H:20]([OH:22])[CH3:21]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[C:7]([O:11][C:12](=[O:17])[CH2:13][CH2:14][CH2:15][NH:18][CH2:19][C@@H:20]([OH:22])[CH3:21])([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2757253tert-Butyl 4-bromobutanoateHCID 7311736(S)-(+)-1-Aminopropan-2-ol

Product 1

HCID 580168024-{[(2S)-2-Hydroxypropyl]amino}butyric acid tert.-butyl ester

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Add 2583 mg (18.69 mmol) potassium carbonate, 2780 mg (12.46 mmol) 4-bromobutyric acid tert.-butyl ester and 184 mg (0.50 mmol) tetra-n-butylammonium iodide to a solution of 936 mg (12.46 mmol) (2S)-1-aminopropan-2-ol in 10 ml THF. Stir the reaction mixture for 48 h at room temperature. After filtering-off the inorganic salts, concentrate the filtrate by vacuum evaporation. Take up the residue in dichloromethane and chromatograph on silica gel (solvent: dichloromethane/methanol/35% aqueous ammonia solution 9:1:0.1). 810 mg (30% of theor.) of the desired product is obtained.

Workup

  1. concentrationAfter filtering-off the inorganic salts, concentrate the filtrate
  2. customby vacuum evaporation

Sources & evidence

ORD record
ord-50324aa4ffee4037b018619e0af62989
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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