2-Methoxypropene → (S)-4-(2-Hydroxy-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

HRID 655546노트

반응식

HRID 655546 반응식
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:15][CH2:16][OH:17])[CH2:13][OH:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:20]([CH3:22])=[CH2:21]>COC(OC)(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([O:8][C:9]([N:11]1[C@@H:12]([CH2:15][CH2:16][OH:17])[CH2:13][O:14][C:20]1([CH3:22])[CH3:21])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 83002-MethoxypropeneHCID 7022411(S)-2-Cbz-aminobutane-1,4-diol

생성물 1

HCID 60098506(S)-4-(2-Hydroxy-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester수율 96%

시약·촉매·용매 2

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 64952,2-Dimethoxypropane용매

실험 절차

A solution of (S)—N-(benzyloxycarbonyl)-2-aminobutane-1,4-diol (8.00 g, 33.4 mmol) and toluene-4-sulfonic acid monohydrate (318 mg, 1.67 mmol) in 2,2-dimethoxypropane (320 mL) was stirred at room temperature, then after 2 h 2-methoxypropene (7.71 g, 107 mmol) was added, then after 72 h the reaction mixture was partitioned between ethyl acetate and sat. aq. sodium hydrogencarbonate solution. The organic layer was dried (MgSO4), filtered, and evaporated. The residue was taken up in dichloromethane (200 mL), then after addition of SiO2 (80 g) and water (4.8 mL) the slurry was stirred for 64 h at room temperature. After dilution with dichloromethane and addition of anhydrous magnesium sulfate, insoluble material was removed by filtration through diatomaceous earth. The filtrate was evaporated and chromatographed (SiO2; heptane/ethyl acetate 1:1) to afford the title compound (8.92 g, 96%). Light yellow oil, MS (ISP)=280.1 (M+H)+.

후처리

  1. customafter 72 h the reaction mixture was partitioned between ethyl acetate and sat. aq. sodium hydrogencarbonate solution
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. additionafter addition of SiO2 (80 g) and water (4.8 mL) the slurry
  6. additionAfter dilution with dichloromethane and addition of anhydrous magnesium sulfate, insoluble material
  7. customwas removed by filtration through diatomaceous earth
  8. customThe filtrate was evaporated
  9. customchromatographed (SiO2; heptane/ethyl acetate 1:1)

출처 및 근거

ORD 기록
ord-566f1c7583c7486f9f3e773a2008d3ff
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071586B2

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