Piperidine → (S)-2-amino-N-(benzo[c][1,2,5]thiadiazol-4-ylmethyl)-3-(4-tert-butoxyphenyl)-N-((S)-1,1-diethoxypropan-2-yl)propanamide

HRID 2362004Notes

Reaction equation

[N:1]1[S:2][N:3]=[C:4]2[C:9]([CH2:10][N:11]([C@@H:45]([CH3:53])[CH:46]([O:50][CH2:51][CH3:52])[O:47][CH2:48][CH3:49])[C:12](=[O:44])[C@@H:13]([NH:26]C(=O)OCC3C4C=CC=CC=4C4C3=CC=CC=4)[CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:17][CH:16]=3)=[CH:8][CH:7]=[CH:6][C:5]=12.N1CCCCC1>>[NH2:26][C@@H:13]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:17][CH:16]=1)[C:12]([N:11]([CH2:10][C:9]1[C:4]2[C:5](=[N:1][S:2][N:3]=2)[CH:6]=[CH:7][CH:8]=1)[C@@H:45]([CH3:53])[CH:46]([O:50][CH2:51][CH3:52])[O:47][CH2:48][CH3:49])=[O:44]

Participants

Reactant 2

HCID 8082Piperidine

HCID 86698532(9H-fluoren-9-yl)methyl(S)-1-((benzo[c][1,2,5]thiadiazol-4-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-3-(4-tert-butoxyphenyl)-1-oxopropan-2-ylcarbamate

Product 1

HCID 67075006(S)-2-amino-N-(benzo[c][1,2,5]thiadiazol-4-ylmethyl)-3-(4-tert-butoxyphenyl)-N-((S)-1,1-diethoxypropan-2-yl)propanamideYield 139.7%

Procedure

According to the procedure described in the synthesis method of Compound IV-1, (9H-fluoren-9-yl)methyl(S)-1-((benzo[c][1,2,5]thiadiazol-4-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-3-(4-tert-butoxyphenyl)-1-oxopropan-2-ylcarbamate (Compound III-8) (509 mg, 0.69 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 (496 mg, 139%).

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-a328cc266d054fd6b297c6bd0e6fd5a2
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691819B2

Reaction notes

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