1,2-Dichloroethane → (2S,3S)-N-cyclopropyl-3-(dibenzylamino)-2-hydroxypentanamide

HRID 1025299Notes

Reaction equation

HRID 1025299 reaction equation
[CH2:1]([N:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@@H:9]([CH2:15][CH3:16])[C@H:10]([OH:14])[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:24]1([NH2:27])[CH2:26][CH2:25]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>O.ClCCl>[CH:24]1([NH:27][C:11](=[O:12])[C@@H:10]([OH:14])[C@@H:9]([N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:15][CH3:16])[CH2:26][CH2:25]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 57872117(2S,3S)-3-(dibenzylamino)-2-hydroxypentanoic acid

Product 1

HCID 44594159(2S,3S)-N-cyclopropyl-3-(dibenzylamino)-2-hydroxypentanamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Under an atmosphere of argon, (2S,3S)-3-(dibenzylamino)-2-hydroxypentanoic acid (5.85 g, 18.7 mmol, Eq: 1.00), cyclopropanamine (2.13 g, 2.62 ml, 37.3 mmol, Eq: 2) were combined with dichloromethane (100 ml) to give a light yellow solution. At 0° C. HOBt (4.29 g, 28.0 mmol, Eq: 1.5), EDC (5.37 g, 28.0 mmol, Eq: 1.5) and N-methylmorpholine (3.78 g, 4.1 ml, 37.3 mmol, Eq: 2) were added to the reaction. The reaction was stirred overnight at RT. The reaction mixture was poured into water (150 ml) and extracted with dichloromethane. The organic layer was back-extracted with water. The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 70 g, 0% to 60% ethyl acetate in heptane). The title compound was obtained as a light brown crystalline (4.42 g, 67.2%, MS (m/e)=353.3 [M+H+]).

Workup

  1. customto give a light yellow solution
  2. customAt 0° C
  3. extractionextracted with dichloromethane
  4. extractionThe organic layer was back-extracted with water
  5. dry with materialThe organic layers were dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography (silica gel, 70 g, 0% to 60% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-41d104bc439b4e0f890efb29f950e53f
Source dataset
uspto-grants-2014_05
Patent number
US08729061B2

Reaction notes

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