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

HRID 1968910
ノート
印刷プレビュー

反応式

HRID 1968910 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

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

生成物 1

HCID 54009748Dibenzyl 4-hydroxy-2,2-dimethylbutyl phosphate収率 17%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-c1c19d8ab2a64037b32306e6142868cd
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08426388B2

反応ノート

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