Triphenylphosphine → N-{2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethyl}-N-methyl-4-nitrobenzenesulfonamide

HRID 216398Notes

Reaction equation

HRID 216398 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[CH3:13][C:14]([CH3:58])([CH2:56][CH3:57])[CH2:15][C:16]1[N:17]=[C:18]([CH2:40][CH:41]([C:43]2[CH:48]=[CH:47][C:46]([C:49]3[CH:54]=[CH:53][C:52]([F:55])=[CH:51][N:50]=3)=[CH:45][CH:44]=2)O)[N:19]([C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=1.[CH3:59][NH:60][S:61]([C:64]1[CH:69]=[CH:68][C:67]([N+:70]([O-:72])=[O:71])=[CH:66][CH:65]=1)(=[O:63])=[O:62].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:13][C:14]([CH3:58])([CH2:56][CH3:57])[CH2:15][C:16]1[N:17]=[C:18]([CH2:40][CH:41]([N:60]([CH3:59])[S:61]([C:64]2[CH:65]=[CH:66][C:67]([N+:70]([O-:72])=[O:71])=[CH:68][CH:69]=2)(=[O:62])=[O:63])[C:43]2[CH:48]=[CH:47][C:46]([C:49]3[CH:54]=[CH:53][C:52]([F:55])=[CH:51][N:50]=3)=[CH:45][CH:44]=2)[N:19]([C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 232993N-Methyl-4-nitrobenzenesulfonamideHCID 5462977Diethyl azodicarboxylateHCID 686683162-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanol

Product 1

HCID 68668057N-{2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethyl}-N-methyl-4-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DEAD (1.3 mL, 8.2 mmol) was added to an ambient temperature solution of 2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanol (2.5 g, 4.1 mmol), N-methyl-4-nitrobenzenesulfonamide (1.8 g, 8.2 mmol) and triphenylphosphine (2.7 g, 10.2 mmol) in tetrahydrofuran (20 mL). After stirring at ambient temperature overnight, the reaction mixture was concentrated. Chromatography over silica eluting with 0-60% ethyl acetate/hexane afforded N-{2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethyl}-N-methyl-4-nitrobenzenesulfonamide.

Workup

  1. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-b83d107b87db4542b773ab32ee592122
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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