tert-Butyl methylsulfonyl{3-[(2S)oxiranylmethoxy]phenyl}carbamate → tert-butyl 3-{[(2S)-3-({4-[(1-{[(4-fluorobenzyl)amino]carbonyl}-4-piperidinyl)amino]phenethyl}amino)-2-hydroxypropyl]oxy}phenyl(methylsulfonyl)carbamate

HRID 1281578Notes

Reaction equation

HRID 1281578 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][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[O:19])[CH2:14][CH2:13]2)=[CH:9][CH:8]=1.[CH3:31][S:32]([N:35]([C:43]1[CH:48]=[CH:47][CH:46]=[C:45]([O:49][CH2:50][C@@H:51]2[CH2:53][O:52]2)[CH:44]=1)[C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])(=[O:34])=[O:33]>C(Cl)(Cl)Cl.CO>[F:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][NH:20][C:18]([N:15]2[CH2:14][CH2:13][CH:12]([NH:11][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][NH:4][CH2:53][C@H:51]([OH:52])[CH2:50][O:49][C:45]4[CH:44]=[C:43]([N:35]([S:32]([CH3:31])(=[O:34])=[O:33])[C:36](=[O:42])[O:37][C:38]([CH3:39])([CH3:40])[CH3:41])[CH:48]=[CH:47][CH:46]=4)=[CH:30][CH:29]=3)[CH2:17][CH2:16]2)=[O:19])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 23381355tert-Butyl methylsulfonyl{3-[(2S)oxiranylmethoxy]phenyl}carbamateHCID 699867244-[4-(2-Aminoethyl)anilino]-N-(4-fluorobenzyl)-1-piperidinecarboxamide formate

Product 1

HCID 70133313tert-butyl 3-{[(2S)-3-({4-[(1-{[(4-fluorobenzyl)amino]carbonyl}-4-piperidinyl)amino]phenethyl}amino)-2-hydroxypropyl]oxy}phenyl(methylsulfonyl)carbamate

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

4-[4-(2-Aminoethyl)anilino]-N-(4-fluorobenzyl)-1-piperidinecarboxamide formate (0.591 g, 1.42 mmol) was reacted with tert-butyl methylsulfonyl{3-[(2S)oxiranylmethoxy]phenyl]carbamate (0.488 g, 1.42 mmol) according to Procedure G (eluant: 20:1 going to 10:1 chloroform-methanol) to give tert-butyl 3-{[(2S)-3-({4-[(1-{[(4-fluorobenzyl)amino]carbonyl}-4-piperidinyl)amino]phenethyl}amino)-2-hydroxypropyl]oxy}phenyl(methylsulfonyl)carbamate which was dissolved in formic acid and stirred at ambient temperature overnight. The solvent was removed in vacuo and the residue purified by flash chromatography on silica gel Merck-60 (eluant: 5:1 chloroform-methanol) to furnish the title compound (0.1 g, 0.163 mmol).

Sources & evidence

ORD record
ord-f2d1fd3b103c452c95a098e9517546fb
Source dataset
uspto-grants-2002_09
Patent number
US06451814B1

Reaction notes

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