(R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole → (S)-[l-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperidin-4-yl]-(4-trifluoromethoxyphenyl)methanone

HRID 856251Notes

Reaction equation

HRID 856251 reaction equation
Cl[C:2]1[N:3]([CH2:10][C@:11]2([CH3:14])[CH2:13][O:12]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[F:15][C:16]([F:33])([F:32])[O:17][C:18]1[CH:31]=[CH:30][C:21]([C:22]([CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[O:23])=[CH:20][CH:19]=1>>[CH3:14][C@@:11]1([CH2:13][N:27]2[CH2:28][CH2:29][CH:24]([C:22]([C:21]3[CH:30]=[CH:31][C:18]([O:17][C:16]([F:15])([F:32])[F:33])=[CH:19][CH:20]=3)=[O:23])[CH2:25][CH2:26]2)[O:12][C:2]2=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]2[CH2:10]1

Participants

3

Reactant 2

HCID 10443353(R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazoleHCID 230814584-(4-Trifluoromethoxybenzoyl)-piperidine

Product 1

HCID 69479814(S)-[l-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperidin-4-yl]-(4-trifluoromethoxyphenyl)methanoneYield 37%

Procedure

Using (R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole prepared in Example 12 (1.0 g, 4.6 mmol) and 4-(4-trifluoromethoxybenzoyl)piperidine (1.3 g, 4.8 mmol) gave (S)-[l-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperidin-4-yl]-(4-trifluoromethoxyphenyl)methanone (771 mg, yield 37%) as a light yellow powder.

Sources & evidence

ORD record
ord-03ac1993f28f4b1daa03accce915849c
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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