Methanol → (S)-2-amino-N-((S)-1,1-diethoxypropan-2-yl)-N-(quinolin-8-ylmethyl)propanamide

HRID 718922Notes

Reaction equation

HRID 718922 reaction equation
[CH2:1]([O:3][CH:4]([O:41][CH2:42][CH3:43])[C@@H:5]([N:7]([CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[C:35]2[C:40]=1[N:39]=[CH:38][CH:37]=[CH:36]2)[C:8](=[O:29])[C@@H:9]([NH:11]C(=O)OCC1C2C=CC=CC=2C2C1=CC=CC=2)[CH3:10])[CH3:6])[CH3:2].N1CCCCC1.CC(=O)OCC.CO>C(Cl)Cl>[NH2:11][C@@H:9]([CH3:10])[C:8]([N:7]([C@@H:5]([CH3:6])[CH:4]([O:41][CH2:42][CH3:43])[O:3][CH2:1][CH3:2])[CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[C:35]2[C:40]=1[N:39]=[CH:38][CH:37]=[CH:36]2)=[O:29]

Participants

6

Reactant 4

HCID 887MethanolHCID 8082PiperidineHCID 8857Ethyl AcetateHCID 86652578(9H-Fluoren-9-yl)methyl (S)-1-(((S)-1,1-diethoxypropan-2-yl)(quinolin-8-ylmethyl)amino)-1-oxopropan-2-ylcarbamate

Product 1

HCID 67075480(S)-2-amino-N-((S)-1,1-diethoxypropan-2-yl)-N-(quinolin-8-ylmethyl)propanamideYield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

(9H-Fluoren-9-yl)methyl (S)-1-(((S)-1,1-diethoxypropan-2-yl)(quinolin-8-ylmethyl)amino)-1-oxopropan-2-ylcarbamate (Compound III-11) 15.7 g (27 mmol) and piperidine 22.7 g (270 mmol) were added in DCM (90 ml). The mixture was stirred for 1.5 h at room temperature. The mixture was diluted with DCM (200 ml) and washed with water (150 ml×3). The solution was concentrated in vacuo. The residue was purified by column chromatography on silica gel with PE:EA=50:1 to DCM:MeOH=10:1 to give the title compound 7.1 g, (yield 73%).

Workup

  1. washwashed with water (150 ml×3)
  2. concentrationThe solution was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel with PE

Sources & evidence

ORD record
ord-bc63c8b27eb040e79592ea62da4acdaf
Source dataset
uspto-grants-2015_11
Patent number
US09193734B2

Reaction notes

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