2-Nitroimidazole → HCID 58721830, compound

HRID 1247529Notes

Reaction equation

HRID 1247529 reaction equation
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[CH3:9][O:10][C:11](=[O:35])[C@H:12]([CH2:33]O)[NH:13][C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[N+:1]([C:4]1[N:5]([CH2:33][C@@H:12]([C:11]([O:10][CH3:9])=[O:35])[NH:13][C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 107012-NitroimidazoleHCID 11776TriphenylphosphineHCID 7128367N-(Triphenylmethyl)-L-serine methyl ester

Product 1

HCID 58721830HCID 58721830, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Di-isopropylazodicarboxylate (1.3 mL, 6.6 mmol) was added dropwise to a solution of 2-nitroimidazole (1.0 g, 9 mmol), N-trityl-L-serine methyl ester (2.0 g, 6 mmol) and triphenylphosphine (1.73 g, 6.6 mmol) in THF (100 mL). The reaction was stirred at ambient temperature for approximately 5 hours The volatiles were removed by evaporation under reduced pressure and the residue purified by column chromatography (EtOAc:isohexane 1:19) to afford the title compound (1.2 g, 44%) as a white solid.

Workup

  1. customwere removed by evaporation under reduced pressure
  2. customthe residue purified by column chromatography (EtOAc:isohexane 1:19)

Sources & evidence

ORD record
ord-6165cfef15b94b97854738d943d266c8
Source dataset
uspto-grants-2006_10
Patent number
US07129249B2

Reaction notes

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