t-Butyl{2-fluoro-4-[(2s)oxiranylmethoxy]phenoxy}diphenylsilane → 4-(4-[2-[(2S)-3-(3-Fluoro-4-hydroxy-phenoxy)-2-hydroxy-propylamino]-ethyl]-phenylamino)-piperidine-1-carboxylic acid octylamide

HRID 396039Notes

Reaction equation

HRID 396039 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.C([Si]([O:48][C:49]1[CH:54]=[CH:53][C:52]([O:55][CH2:56][C@@H:57]2[CH2:59][O:58]2)=[CH:51][C:50]=1[F:60])(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C>C(Cl)(Cl)Cl.CO>[CH2:21]([NH:20][C:18]([N:15]1[CH2:16][CH2:17][CH:12]([NH:11][C:10]2[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][NH:4][CH2:59][C@H:57]([OH:58])[CH2:56][O:55][C:52]3[CH:53]=[CH:54][C:49]([OH:48])=[C:50]([F:60])[CH:51]=3)=[CH:30][CH:29]=2)[CH2:13][CH2:14]1)=[O:19])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 23381349t-Butyl{2-fluoro-4-[(2s)oxiranylmethoxy]phenoxy}diphenylsilaneHCID 699872524-[4-(2-Aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide formate

Product 1

HCID 102312594-(4-[2-[(2S)-3-(3-Fluoro-4-hydroxy-phenoxy)-2-hydroxy-propylamino]-ethyl]-phenylamino)-piperidine-1-carboxylic acid octylamideYield 31.1%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

4-[4-(2-Aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide formate (0.376 g, 0.87 mmol) was reacted with tert-butyl{2-fluoro-4-[(2S)oxiranylmethoxy]phenoxy}diphenylsilane (0.368 g, 0.87 mmol) according to Procedure G (eluant: 20:1 chloroform-methanol) to give the title compound (0.228 g, 0.271 mmol).

Sources & evidence

ORD record
ord-6e9618c287544242a011e076bb6a68e7
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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