Sodium Hydroxide → (S)-(-)-2-Nitro-1-(2-oxiranylmethyl)-1H-imidazole

Reaction equation

Cl[CH2:2][C@@H:3]([OH:13])[CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[C:6]1[N+:10]([O-:12])=[O:11].[OH-].[Na+]>>[N+:10]([C:6]1[N:5]([CH2:4][C@H:3]2[CH2:2][O:13]2)[CH:9]=[CH:8][N:7]=1)([O-:12])=[O:11]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 11052772(S)-(+)-alpha-(chloromethyl)-2-nitro-1H-imidazole-1-ethanol

Product 1

HCID 11768967(S)-(-)-2-Nitro-1-(2-oxiranylmethyl)-1H-imidazoleYield 65.1%

Procedure

Alternatively, reaction of 0.56 g of (S)-(+)-α-(chloromethyl)-2-nitro-1H-imidazole-1-ethanol with 3 mL of 10% aqueous sodium hydroxide at 25° C. for 30 minutes followed by further processing as above gives 0.3 g of the product.

Sources & evidence

ORD record: ord-5a913f352473456ca2e57a3f7631e7b4
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05652255

Reaction notes

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