Piperidine → (S)-2-amino-N-((S)-1,1-diethoxypropan-2-yl)-3-(4-hydroxy-2,6-dimethylphenyl)-N-(quinolin-8-ylmethyl)propanamide

HRID 2274693Notes

Reaction equation

[CH2:1]([O:3][CH:4]([O:50][CH2:51][CH3:52])[C@@H:5]([N:7]([CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[C:44]2[C:49]=1[N:48]=[CH:47][CH:46]=[CH:45]2)[C:8](=[O:38])[C@@H:9]([NH:20]C(=O)OCC1C2C=CC=CC=2C2C1=CC=CC=2)[CH2:10][C:11]1[C:16]([CH3:17])=[CH:15][C:14]([OH:18])=[CH:13][C:12]=1[CH3:19])[CH3:6])[CH3:2].N1CCCCC1>>[NH2:20][C@@H:9]([CH2:10][C:11]1[C:16]([CH3:17])=[CH:15][C:14]([OH:18])=[CH:13][C:12]=1[CH3:19])[C:8]([N:7]([C@@H:5]([CH3:6])[CH:4]([O:50][CH2:51][CH3:52])[O:3][CH2:1][CH3:2])[CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[C:44]2[C:49]=1[N:48]=[CH:47][CH:46]=[CH:45]2)=[O:38]

Participants

Reactant 2

HCID 8082Piperidine

HCID 86698531(9H-fluoren-9-yl)methyl (S)-1-(((S)-1,1-diethoxypropan-2-yl)(quinolin-8-ylmethyl)amino)-3-(4-hydroxy-2,6-dimethylphenyl)-1-oxopropan-2-ylcarbamate

Product 1

HCID 67088322(S)-2-amino-N-((S)-1,1-diethoxypropan-2-yl)-3-(4-hydroxy-2,6-dimethylphenyl)-N-(quinolin-8-ylmethyl)propanamideYield 115.4%

Procedure

According to the procedure described in the synthesis method of Compound IV-1, (9H-fluoren-9-yl)methyl(S)-1-(((S)-1,1-diethoxypropan-2-yl)(quinolin-8-ylmethyl)amino)-3-(4-hydroxy-2,6-dimethylphenyl)-1-oxopropan-2-ylcarbamate (Compound III-18) (512 mg, 0.73 mmol) was treated with piperidine and the obtained residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=9:1, chloroform:methanol=100:0 and 8:2) to obtain the title compound (404 mg, 115%).

Workup

customthe obtained residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=9:1, chloroform:methanol=100:0 and 8:2)

Sources & evidence

ORD record: ord-4bcd852785f948c08bc889e3a2077688
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126981B2

Reaction notes

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