t-butyl(diphenyl)silyl 3-chloro-4-[(2S)oxiranylmethoxy]phenyl ether → 4-[4-(2-{[(2S)-3-(2-Chloro-4-hydroxyphenoxy)-2-hydroxypropyl]amino}ethyl)anilino]-N-octyl-1-piperidinecarboxamide

HRID 1281499Notes

Reaction equation

HRID 1281499 reaction equation
C(O)=O.[NH2:4][CH2:5][CH2:6][C:7]1[CH:30]=[CH:29][C:10]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:19])[CH2:14][CH2:13]2)=[CH:9][CH:8]=1.[Cl:31][C:32]1[CH:33]=[C:34]([O:43][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:35]=[CH:36][C:37]=1[O:38][CH2:39][C@@H:40]1[CH2:42][O:41]1>C(Cl)(Cl)Cl.CO>[Cl:31][C:32]1[CH:33]=[C:34]([OH:43])[CH:35]=[CH:36][C:37]=1[O:38][CH2:39][C@@H:40]([OH:41])[CH2:42][NH:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:19])[CH2:14][CH2:13]2)=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 23381354t-butyl(diphenyl)silyl 3-chloro-4-[(2S)oxiranylmethoxy]phenyl etherHCID 699872524-[4-(2-Aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide formate

Product 1

HCID 102317664-[4-(2-{[(2S)-3-(2-Chloro-4-hydroxyphenoxy)-2-hydroxypropyl]amino}ethyl)anilino]-N-octyl-1-piperidinecarboxamideYield 17%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

4-[4-(2-Aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide formate (0.57 g, 1.35 mmol) was reacted with tert-butyl(diphenyl)silyl 3-chloro-4-[(2S)oxiranyl-methoxy]phenyl ether (0.59 g, 1.35 mmol) according to Procedure G (eluant: 20:1 chloroform-methanol) to give the title compound (0.185 g, 0.23 mmol).

Sources & evidence

ORD record
ord-64fb9257f293400f938e5d1b13a511a0
Source dataset
uspto-grants-2002_09
Patent number
US06451814B1

Reaction notes

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