2,4,6-Triisopropylbenzenesulfonyl azide → HCID 10407303, 화합물

HRID 133842

반응식

HRID 133842 반응식
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:25])[CH2:15][C:16]([CH3:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K].CC(C1C=C(C(C)C)C(S([N:42]=[N+:43]=[N-:44])(=O)=O)=C(C(C)C)C=1)C>O1CCCC1.C1(C)C=CC=CC=1>[N:42]([C@@H:15]([C:16]([CH3:17])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:24])[C:14]([N:9]1[C@@H:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:12][O:11][C:10]1=[O:13])=[O:25])=[N+:43]=[N-:44]

참가 물질

6

반응물 3

HCID 3717072,4,6-Triisopropylbenzenesulfonyl azideHCID 5462222PotassiumHCID 10472250HCID 10472250, 화합물

생성물 1

HCID 10407303HCID 10407303, 화합물수율 96.9%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of (4S)-4-benzyl-3-(3-methyl-3-phenylbutanoyl)-1,3-oxazolidin-2-one (1.0 g, 3.0 mmol, from Reference Example 26) in anhydrous tetrahydrofuran (16 mL) is cooled to −78° C. in a dry-ice/acetone bath while stirring under a nitrogen atmosphere. Potassium hexamethylsilazide (0.5 M solution in toluene, 6.6 mL, 3.3 mmol) is added dropwise to the solution via syringe. After stirring for 1 hour at −78° C., trisyl azide (1.2 g, 3.8 mmol) in tetrahydrofuran (8 mL) is added dropwise. The reaction mixture is stirred for 2-3 minutes at −78° C. and then quenched by the addition of glacial acetic acid (0.8 mL). Stirring is continued for 1 hour at 40° C. The reaction mixture is diluted with brine and diethyl ether. The aqueous phase is extracted thrice with diethyl ether. The combined extracts are washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride, dried over sodium sulfate, decanted, and concentrated under reduced pressure to afford a white/yellow solid. The crude material is purified by flash chromatography (ethyl acetate/hexanes) to afford a clear, straw colored oil (1.1 g, 79%). TOF MS (ES+): (M+H)=379.2

후처리

  1. stirringAfter stirring for 1 hour at −78° C.
  2. stirringThe reaction mixture is stirred for 2-3 minutes at −78° C.
  3. customquenched by the addition of glacial acetic acid (0.8 mL)
  4. stirringStirring
  5. additionThe reaction mixture is diluted with brine and diethyl ether
  6. extractionThe aqueous phase is extracted thrice with diethyl ether
  7. washThe combined extracts are washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride
  8. dry with materialdried over sodium sulfate
  9. customdecanted
  10. concentrationconcentrated under reduced pressure
  11. customto afford a white/yellow solid
  12. customThe crude material is purified by flash chromatography (ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-a2d6f9d651e540708234ef0796a29fa6
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390910B2

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