(R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole → HCID 69635327, compound

HRID 856268Notes

Reaction equation

HRID 856268 reaction equation
[Cl:1][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.[NH:15]1[CH2:20][CH2:19][CH:18]([N:21]([CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=2)[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:17][CH2:16]1>>[Cl:1][C:2]1[N:3]([CH2:10][C@:11]([OH:12])([CH3:14])[CH2:13][N:15]2[CH2:20][CH2:19][CH:18]([N:21]([CH2:29][CH2:30][C:31]3[CH:32]=[CH:33][C:34]([C:37]([F:38])([F:39])[F:40])=[CH:35][CH:36]=3)[C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:27])[CH3:25])[CH2:17][CH2:16]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

3

Reactant 2

HCID 10443353(R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazoleHCID 23081307HCID 23081307, compound

Product 1

HCID 69635327HCID 69635327, compoundYield 70.4%

Procedure

Using (R)-2-chloro-1-(2-methyloxiran-2-yl-methyl)-4-nitroimidazole prepared in Example 12 (0.332 g, 0.891 mmol) and tert-butyl piperidin-4-yl-N-[2-(4-trifluoromethylphenyl)ethyl]carbamate (0.194 g, 0.891 mmol) gave tert-butyl (S)-{1-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]piperidin-4-yl}-N-[2-(4-trifluoromethylphenyl)-ethyl]carbamate (0.370 g, yield 70%) as a light yellow oil in the same manner as in Example 277.

Sources & evidence

ORD record
ord-a117b51b3f4b4be69f3a1ea8b410278a
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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