2-Nitroimidazole → 5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-[2-(2-nitro-1H-imidazol-1-yl)ethyl]-1,3-dioxane

HRID 514637Notes

Reaction equation

[O:1]([CH2:19][C:20]1([CH2:28][CH2:29]O)[CH2:25][O:24][C:23]([CH3:27])([CH3:26])[O:22][CH2:21]1)[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[N+:64]([C:67]1[NH:68][CH:69]=[CH:70][N:71]=1)([O-:66])=[O:65]>O1CCCC1>[O:1]([CH2:19][C:20]1([CH2:28][CH2:29][N:68]2[CH:69]=[CH:70][N:71]=[C:67]2[N+:64]([O-:66])=[O:65])[CH2:21][O:22][C:23]([CH3:27])([CH3:26])[O:24][CH2:25]1)[Si:2]([C:15]([CH3:17])([CH3:18])[CH3:16])([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 25 °C

Procedure

48 mg (0.112 mmol equivalents) of 5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-hydroxyethyl-1,3-dioxane was dissolved in 1 mL of tetrahydrofuran, 32 mg (0.123 mmol equivalents) of triphenylphosphine, 24 μL (0.123 mmol equivalents) of diisopropyl azodicarboxylate, and 38 mg (0.336 mmol equivalents) of 2-nitroimidazole were added thereto, and the mixture was stirred at room temperature (25° C.) for 4 hours. After completion of the reaction, the mixture was concentrated under vacuum, and the obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=4/1) to give 46 mg (0.088 mmol equivalents) of 5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-[2-(2-nitro-1H-imidazol-1-yl)ethyl]-1,3-dioxane.

Workup

customAfter completion of the reaction
concentrationthe mixture was concentrated under vacuum
customthe obtained crude product
customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=4/1)

Sources & evidence

ORD record: ord-d829a5a7a34c4290998d5908fe7623f1
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09107964B2

Reaction notes

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