4-{[4-(2-{[(2S)-3-(4-([tert-Butyl(diphenyl)silyl]oxy}phenoxy)-2-hydroxy-propyl]amino}ethyl)phenyl]sulfanyl}-N-phenyl-1-piperidinecarboxamide → 4-(4-[2-[(2S)-2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-phenylsulfanyl)-piperidine-1-carboxylic acid phenylamide

HRID 396020Notes

Reaction equation

HRID 396020 reaction equation
[Si]([O:18][C:19]1[CH:54]=[CH:53][C:22]([O:23][CH2:24][C@@H:25]([OH:52])[CH2:26][NH:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([S:36][CH:37]3[CH2:42][CH2:41][N:40]([C:43]([NH:45][C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)=[O:44])[CH2:39][CH2:38]3)=[CH:32][CH:31]=2)=[CH:21][CH:20]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>ClCCl.C(Cl)(Cl)Cl.CO>[C:46]1([NH:45][C:43]([N:40]2[CH2:41][CH2:42][CH:37]([S:36][C:33]3[CH:34]=[CH:35][C:30]([CH2:29][CH2:28][NH:27][CH2:26][C@H:25]([OH:52])[CH2:24][O:23][C:22]4[CH:53]=[CH:54][C:19]([OH:18])=[CH:20][CH:21]=4)=[CH:31][CH:32]=3)[CH2:38][CH2:39]2)=[O:44])[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1

Participants

3

Reactant 1

HCID 699868494-{[4-(2-{[(2S)-3-(4-([tert-Butyl(diphenyl)silyl]oxy}phenoxy)-2-hydroxy-propyl]amino}ethyl)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 69.7%

Reagents, catalysts & solvents 1

HCID 86584582Dichloromethane chloroform methanolSolvent

Procedure

4-{[4-(2-{[(2S)-3-(4-{[tert-Butyl(diphenyl)silyl]oxy}phenoxy)-2-hydroxy-propyl]amino}ethyl)phenyl]sulfanyl}-N-phenyl-1-piperidinecarboxamide (0.25 g, 0.33 mmol) was reacted according to Procedure H (eluant: 12:3:1 dichloromethane-chloroform-methanol) to give the title compound (0.12 g, 0.23 mmol).

Sources & evidence

ORD record
ord-e9a025848c7b4fd19a9d3eefee0ad603
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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