Piperidine → (S)-2-amino-N-(benzo[b]thiophen-3-ylmethyl)-3-(4-tert-butoxyphenyl)-N-((S)-1,1-diethoxypropan-2-yl)propanamide

HRID 1254515Notes

Reaction equation

[S:1]1[CH:5]=[C:4]([CH2:6][N:7]([C@@H:41]([CH3:49])[CH:42]([O:46][CH2:47][CH3:48])[O:43][CH2:44][CH3:45])[C:8](=[O:40])[C@@H:9]([NH:22]C(=O)OCC2C3C=CC=CC=3C3C2=CC=CC=3)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:13][CH:12]=2)[C:3]2[CH:50]=[CH:51][CH:52]=[CH:53][C:2]1=2.N1CCCCC1>>[NH2:22][C@@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[CH:13][CH:12]=1)[C:8]([N:7]([CH2:6][C:4]1[C:3]2[CH:50]=[CH:51][CH:52]=[CH:53][C:2]=2[S:1][CH:5]=1)[C@@H:41]([CH3:49])[CH:42]([O:46][CH2:47][CH3:48])[O:43][CH2:44][CH3:45])=[O:40]

Participants

Reactant 2

HCID 8082Piperidine

HCID 86698528(9H-fluoren-9-yl)methyl (S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-3-(4-tert-butoxyphenyl)-1-oxopropan-2-ylcarbamate

Product 1

HCID 67075252(S)-2-amino-N-(benzo[b]thiophen-3-ylmethyl)-3-(4-tert-butoxyphenyl)-N-((S)-1,1-diethoxypropan-2-yl)propanamideYield 98%

Procedure

According to the procedure described in the synthesis method of Compound IV-1, (9H-fluoren-9-yl)methyl (S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-3-(4-tert-butoxyphenyl)-1-oxopropan-2-ylcarbamate (Compound III-6) 500 mg (0.68 mmol) was treated with piperidine and purified on silica gel column chromatography (n-hexane:ethyl acetate=9:1, chloroform:methanol=100:0 and 8:2) to obtain the title compound 339 mg (98%).

Workup

custompurified on silica gel column chromatography (n-hexane:ethyl acetate=9:1, chloroform:methanol=100:0 and 8:2)

Sources & evidence

ORD record: ord-36b909d83ba648b3a760a0f9d24b296f
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455488B2

Reaction notes

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