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

HRID 514625

반응식

HRID 514625 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 142273Oxoosmium촉매2회HCID 218864351,4-Dioxane--water (1/1)용매

반응 조건

온도
25 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-29368c36a14447379a31d001f7ba8fc9
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09107964B2

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