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Sodium Iodate → 5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-[(4-formyl-2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane

HRID 514625
Notes
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Reaction equation

HRID 514625 reaction equation
[O:1]([CH2:19][C:20]1([CH2:28][N:29]2[CH:33]=[C:32]([CH:34]=C)[N:31]=[C:30]2[N+:36]([O-:38])=[O:37])[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.I([O-])(=O)=[O:40].[Na+]>[Os]=O.O.O1CCOCC1>[O:1]([CH2:19][C:20]1([CH2:28][N:29]2[CH:33]=[C:32]([CH:34]=[O:40])[N:31]=[C:30]2[N+:36]([O-:38])=[O:37])[CH2:25][O:24][C:23]([CH3:27])([CH3:26])[O:22][CH2:21]1)[Si:2]([C:15]([CH3:16])([CH3:18])[CH3:17])([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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 23675764Sodium IodateHCID 903004335-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-[(4-vinyl-2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane

Product 1

HCID 903003755-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-[(4-formyl-2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxaneYield 66.7%

Reagents, catalysts & solvents 2

HCID 142273OxoosmiumCatalyst2×
HCID 21886435
1,4-Dioxane--water (1/1)
Solvent

Conditions

Temperature
25 °C

Procedure

2.0 mL of a mixed solution of water/1,4-dioxane=3/1 was added to 163 mg (0.30 mmol equivalents) of 5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-[(4-vinyl-2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane, 38 mg (microcapsules, Wako Pure Chemical Industries, Ltd., 0.015 mmol equivalents) of osmium oxide and 130 mg (0.60 mmol equivalents) of sodium iodate were added thereto, and the mixture was stirred at room temperature (25° C.) for 5 days. After completion of the reaction, the osmium oxide was taken out, and the reaction liquid was extracted three times with ethyl acetate. The combined ethyl acetate layers were washed with water and brine, then dried with anhydrous magnesium sulfate, and subsequently concentrated under vacuum. The obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=5/1) to give 107 mg (0.20 mmol equivalents) of 5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-[(4-formyl-2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane.

Workup

  1. additionwere added
  2. customAfter completion of the reaction
  3. customthe reaction liquid
  4. extractionwas extracted three times with ethyl acetate
  5. washThe combined ethyl acetate layers were washed with water and brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationsubsequently concentrated under vacuum
  8. customThe obtained crude product
  9. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=5/1)

Sources & evidence

ORD record
ord-29368c36a14447379a31d001f7ba8fc9
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09107964B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes