Tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenylsilane → 4-(4-{2-[(2S)-2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-phenylamino)-piperidine-1-carboxylic Acid [2-(3-methoxy-phenyl)-ethyl]-amide

HRID 395980Notes

Reaction equation

HRID 395980 reaction equation
C(O)=O.[NH2:4][CH2:5][CH2:6][C:7]1[CH:32]=[CH:31][C:10]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=3)=[O:19])[CH2:14][CH2:13]2)=[CH:9][CH:8]=1.C([Si]([O:50][C:51]1[CH:56]=[CH:55][C:54]([O:57][CH2:58][CH:59]2[CH2:61][O:60]2)=[CH:53][CH:52]=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C>C(Cl)(Cl)Cl.CO>[CH3:30][O:29][C:25]1[CH:24]=[C:23]([CH2:22][CH2:21][NH:20][C:18]([N:15]2[CH2:14][CH2:13][CH:12]([NH:11][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][NH:4][CH2:61][C@H:59]([OH:60])[CH2:58][O:57][C:54]4[CH:55]=[CH:56][C:51]([OH:50])=[CH:52][CH:53]=4)=[CH:32][CH:31]=3)[CH2:17][CH2:16]2)=[O:19])[CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 12045564Tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenylsilaneHCID 699871834-[4-(2-Aminoethyl)anilino]-N-(3-methoxyphenethyl)-1-piperidine-carboxamide formate

Product 1

HCID 101879354-(4-{2-[(2S)-2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-phenylamino)-piperidine-1-carboxylic Acid [2-(3-methoxy-phenyl)-ethyl]-amideYield 19.7%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

4-[4-(2-Aminoethyl)anilino]-N-(3-methoxyphenethyl)-1-piperidine-carboxamide formate (0.398 g, 0.899 mmol) was reacted with tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenyl-silane (0.290 g, 0.71 mmol) according to Procedure G to yield (eluant: 20:1 chloroform-methanol) the title compound (0.110 g, 0.14 mmol)

Sources & evidence

ORD record
ord-e2a6de6009bb4f218e330f270aea4e08
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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