Toluene → (S)-4-(2-Hydroxy-2-methylpropyl)oxazolidin-2-one

HRID 1620925

반응식

HRID 1620925 반응식
C[Mg]Br.[C:4]1([CH3:10])[CH:9]=C[CH:7]=[CH:6][CH:5]=1.C1C[O:14]CC1.[O:16]=[C:17]1[NH:21][C@@H](CC(OCC2C=CC=CC=2)=O)C[O:18]1>C(O)(=O)C.O>[OH:14][C:4]([CH3:10])([CH3:9])[CH2:5][C@H:6]1[CH2:7][O:18][C:17](=[O:16])[NH:21]1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 8028Tetrahydrofuran2회HCID 11241814(S)-Benzyl 2-(2-oxooxazolidin-4-YL)acetateHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 11321109(S)-4-(2-Hydroxy-2-methylpropyl)oxazolidin-2-one

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

Methylmagnesium bromide (227 mL of 3M solution in diethyl ether) was added to a mixture of toluene (340 mL) and THF (340 mL) at −20° C. A warm THF solution (170 mL) of the ester from Step 2 (40 g) was then added dropwise maintaining the temperature below −10° C. The mixture was aged for 2 hours and was then slowly added to a mixture of water (1000 mL) and acetic acid (200 mL) and the resultant mixture was stirred for 2 hours at room temperature. The aqueous layer was separated and the organic layer was extracted with water (2×200 mL). The product was extracted from the combined aqueous layers using dichloromethane and a continuous extractor. The dichloromethane extract was evaporated to dryness using heptane as a co-solvent to azeotrope off the acetic acid. The residue was purified by chromatography on SiO2 using ethanol and dichloromethane (1:30) to yield (4S)-4-(2-hydroxy-2-methylpropyl)-1,3-oxazolidin-2-one.

후처리

  1. temperaturemaintaining the temperature below −10° C
  2. customThe aqueous layer was separated
  3. extractionthe organic layer was extracted with water (2×200 mL)
  4. extractionThe product was extracted from the combined aqueous layers
  5. extractionThe dichloromethane extract
  6. customwas evaporated to dryness
  7. customThe residue was purified by chromatography on SiO2

출처 및 근거

ORD 기록
ord-7754505be25e48b09c7d441897047589
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772336B2

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