(2S)-3-[4-benzyloxy-3-(methanesulfonylamino)phenoxy]-1,2-epoxypropane → 4-(4-[2-[(2s)-2-Hydroxy-3-(4-hydroxy-3-methanesulfonylamino-phenoxy)-propylamino]-ethyl]-phenylamino)-piperidine-1-carboxylic acidoctylamide

HRID 396041Notes

Reaction equation

HRID 396041 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([O:38][C:39]1[CH:44]=[CH:43][C:42]([O:45][CH2:46][C@@H:47]2[CH2:49][O:48]2)=[CH:41][C:40]=1[NH:50][S:51]([CH3:54])(=[O:53])=[O:52])C1C=CC=CC=1>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][CH2:49][C@H:47]([OH:48])[CH2:46][O:45][C:42]3[CH:43]=[CH:44][C:39]([OH:38])=[C:40]([NH:50][S:51]([CH3:54])(=[O:53])=[O:52])[CH:41]=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 53819537(2S)-3-[4-benzyloxy-3-(methanesulfonylamino)phenoxy]-1,2-epoxypropaneHCID 699872524-[4-(2-Aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide formate

Product 1

HCID 101682414-(4-[2-[(2s)-2-Hydroxy-3-(4-hydroxy-3-methanesulfonylamino-phenoxy)-propylamino]-ethyl]-phenylamino)-piperidine-1-carboxylic acidoctylamideYield 19%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

4-[4-(2-Aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide formate (0.516 g, 1.2 mmol) was reacted with N-{2-(benzyloxy)-5-[(2S)oxiranylmethoxy]phenyl) methanesulfonamide (prepared according to patent WO9604233) (0.38 g, 1.09 mmol) according to Procedure G (eluant: 20:1 chloroform-methanol) to give the title compound (0.15 g, 0.207 mmol).

Sources & evidence

ORD record
ord-a50f49cebeb945ad80586ab721fa0c57
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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