(2S)-2-{[4-(benzyloxy)phenoxy]methyl}oxirane → 4-[Acetyl-(4-{2-[(2S)-2-hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-phenyl)-amino]-piperidine-1-carboxylic acid octylamide

HRID 395984Notes

Reaction equation

HRID 395984 reaction equation
C(O)=O.[C:4]([N:7]([CH:17]1[CH2:22][CH2:21][N:20]([C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:24])[CH2:19][CH2:18]1)[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][NH2:16])=[CH:10][CH:9]=1)(=[O:6])[CH3:5].C([O:41][C:42]1[CH:52]=[CH:51][C:45]([O:46][CH2:47][C@@H:48]2[CH2:50][O:49]2)=[CH:44][CH:43]=1)C1C=CC=CC=1>>[CH2:26]([NH:25][C:23]([N:20]1[CH2:19][CH2:18][CH:17]([N:7]([C:4](=[O:6])[CH3:5])[C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][NH:16][CH2:50][C@H:48]([OH:49])[CH2:47][O:46][C:45]3[CH:51]=[CH:52][C:42]([OH:41])=[CH:43][CH:44]=3)=[CH:10][CH:9]=2)[CH2:22][CH2:21]1)=[O:24])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

3

Reactant 2

HCID 11817709(2S)-2-{[4-(benzyloxy)phenoxy]methyl}oxiraneHCID 699856224-[Acetyl-4-(2-aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide formate

Product 1

HCID 101210514-[Acetyl-(4-{2-[(2S)-2-hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-phenyl)-amino]-piperidine-1-carboxylic acid octylamideYield 28.3%

Procedure

4-[Acetyl-4-(2-aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide formate (0.25 g, 0.59 mmol) was reacted with (2S)-2-{[4-(benzyloxy)phenoxy]methyl}oxirane (0.137 g, 0.53 mmol) according to Procedure G to give the title compound (eluant: 20:1 chloroform-methanol) (0.1 g, 0.15 mmol).

Sources & evidence

ORD record
ord-28132854f3164c54a41de0ab80ea5313
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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