2-Oxazolidinone → (S)-(-)-alpha-[[(2-Bromoethyl)amino]methyl]-2-nitro-1H-imidazole-1-ethanol, monohydrobromide

HRID 1743046Notes

Reaction equation

[BrH:1].[N+:2]([C:5]1[N:6]([CH2:10][CH2:11][OH:12])[CH:7]=[CH:8][N:9]=1)([O-:4])=[O:3].[N+]([C:16]1N(C[C@H]2CO2)[CH:18]=[CH:19][N:20]=1)([O-])=O.O1CCNC1=O.C[Si](C)(C)[O-].[K+]>>[BrH:1].[Br:1][CH2:18][CH2:19][NH:20][CH2:16][C@H:11]([OH:12])[CH2:10][N:6]1[CH:7]=[CH:8][N:9]=[C:5]1[N+:2]([O-:4])=[O:3]

Participants

Reactant 4

HCID 739492-Oxazolidinone

HCID 11768967(S)-(-)-2-Nitro-1-(2-oxiranylmethyl)-1H-imidazole

HCID 23668039Potassium trimethylsilanolate

HCID 1317186552-nitro-1H-imidazole-1-ethanol, monohydrobromide

Product 1

HCID 131718654(S)-(-)-alpha-[[(2-Bromoethyl)amino]methyl]-2-nitro-1H-imidazole-1-ethanol, monohydrobromide

Procedure

A process for preparing (R)-(+)-α-[[2-bromoethyl)-amino]methyl]-2-nitro-1H-imidazole-1-ethanol, monohydrobromide which comprises reacting (S)-2-nitro-1-(2-oxiranylmethyl)-1H-imidazole with a 2-oxazolidinone of the formula ##STR15## in the presence of potassium trimethylsilanolate to give the (S)- enantiomer of a compound of the formula ##STR16## which is treated with hydrobromic acid in the presence of acetic acid.

Sources & evidence

ORD record: ord-338b5779f701441b8cb1eb861a4217e3
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05342959

Reaction notes

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