t-butyl-[4-(2S)-oxiranylmethoxy-phenoxy]-diphenylsilane → 4-(4-[2-[(2S)-2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-phenylsulfanyl)-piperidine-1-carboxylic acid phenylamide

HRID 396019Notes

Reaction equation

HRID 396019 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:18])[CH2:13][CH2:12]2)=[CH:6][CH:5]=1.C([Si]([O:43][C:44]1[CH:49]=[CH:48][C:47]([O:50][CH2:51][C@@H:52]2[CH2:54][O:53]2)=[CH:46][CH:45]=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C>ClCCl.C(Cl)(Cl)Cl.CO>[C:20]1([NH:19][C:17]([N:14]2[CH2:15][CH2:16][CH:11]([S:10][C:7]3[CH:6]=[CH:5][C:4]([CH2:3][CH2:2][NH:1][CH2:54][C@H:52]([OH:53])[CH2:51][O:50][C:47]4[CH:48]=[CH:49][C:44]([OH:43])=[CH:45][CH:46]=4)=[CH:9][CH:8]=3)[CH2:12][CH2:13]2)=[O:18])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 11327180t-butyl-[4-(2S)-oxiranylmethoxy-phenoxy]-diphenylsilaneHCID 181736014-{[4-(2-Aminoethyl)phenyl]sulfanyl}-N-phenyl-1-piperidinecarboxamide

Product 1

HCID 101428094-(4-[2-[(2S)-2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-phenylsulfanyl)-piperidine-1-carboxylic acid phenylamideYield 26%

Reagents, catalysts & solvents 1

HCID 86584582Dichloromethane chloroform methanolSolvent

Procedure

4-{[4-(2-Aminoethyl)phenyl]sulfanyl}-N-phenyl-1-piperidinecarboxamide (0.45 g, 1.27 mmol) was reacted with tert-butyl{4-[(2S)oxiranylmethoxy]phenoxy}diphenylsilane (0.512 g, 1.27 mmol) according to Procedure G (eluant: 12:3:1 dichloromethane-chloroform-methanol) to give the title compound (0.25 g, 0.33 mmol).

Sources & evidence

ORD record
ord-2f7e1a799e644a5bb204d9323e131cbc
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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