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Sodium Carbonate → Dibenzyl 4-hydroxy-2,2-dimethylbutyl phosphate

HRID 1968910
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HRID 1968910 반응식
[CH3:1][C:2]([CH3:8])([CH2:5][CH2:6][OH:7])[CH2:3][OH:4].N1C=NN=N1.C(N(CC)[P:17]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)C.ClC1C=CC=C(C(OO)=[O:44])C=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.ClCCl>[P:17]([O:4][CH2:3][C:2]([CH3:8])([CH3:1])[CH2:5][CH2:6][OH:7])([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:44]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 5066231Dibenzyl diethylphosphoramiditeHCID 108878792,2-Dimethylbutane-1,4-diolHCID 178418441HCID 178418441, 화합물

생성물 1

HCID 54009748Dibenzyl 4-hydroxy-2,2-dimethylbutyl phosphate수율 17%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of the product from Example 9A (0.80 g, 6.8 mmol) and 1H-tetrazole (0.190 g) in THF (7.0 mL) at 0° C. was added dibenzyl diethylphosphoramidite (0.96 mL), and the solution was allowed to warm to room temperature and was stirred for 68 hours. To this solution was added dichloromethane (7.0 mL) and the mixture was cooled to −45° C., followed by addition of m-chloroperbenzoic acid (1.3 g). The mixture was stirred at −45° C. for 1 hour and at room temperature for 1 hour. 10% Na2CO3 was added and the reaction was extracted twice with chloroform. The combined organic layer was dried over MgSO4, filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with a gradient of 50-100% ethyl acetate in chloroform, to give the title compound (0.396 g, 17%).

후처리

  1. temperaturethe mixture was cooled to −45° C.
  2. stirringThe mixture was stirred at −45° C. for 1 hour and at room temperature for 1 hour
  3. extractionthe reaction was extracted twice with chloroform
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel
  8. washeluting with a gradient of 50-100% ethyl acetate in chloroform

출처 및 근거

ORD 기록
ord-c1c19d8ab2a64037b32306e6142868cd
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08426388B2

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