Isopropanol → cis-5-[3,5-Bis(trifluoromethyl)phenyl]-4-ethenyl-1,3-oxazolidin-2-one

HRID 529697노트

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HRID 529697 반응식
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([C@@H:13]([OH:21])[C@H:14]([CH:19]=[CH2:20])C(NN)=O)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[N:24](OC(C)(C)C)=O.C[CH:32]([OH:34])C>Cl>[F:11][C:9]([F:10])([F:12])[C:7]1[CH:6]=[C:5]([C@H:13]2[O:21][C:32](=[O:34])[NH:24][C@H:14]2[CH:19]=[CH2:20])[CH:4]=[C:3]([C:2]([F:22])([F:1])[F:23])[CH:8]=1

참가 물질

5

반응물 3

HCID 3776Isopropanol2회HCID 10906Tert-Butyl nitriteHCID 86682260(2S)-2-[(S)-[3,5-Bis(trifluoromethyl)phenyl](hydroxy)methyl]but-3-enehydrazide

생성물 1

HCID 86682259cis-5-[3,5-Bis(trifluoromethyl)phenyl]-4-ethenyl-1,3-oxazolidin-2-one

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

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온도
50 °C

실험 절차

(2S)-2-[(S)-[3,5-Bis(trifluoromethyl)phenyl](hydroxy)methyl]but-3-enehydrazide (14.5 g, 42.4 mmol) was dissolved in IPA (100 mL) and HCl (4N in dioxane, 20 mL). tert-Butyl nitrite (5.24 g, 50.8 mmol) in IPA (20 mL) was added via a syringe pump at 50° C. over 1 hr. The reaction mixture was stirred at 50° C. and additional hour and the volatiles were removed. The crude mixture was dissolved in ethyl acetate (150 mL), washed with aqueous Na2CO3 (100 mL), dried over sodium sulfate, filtered and concentrated. The resultant oil was purified by column chromatography to yield (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-ethenyl-1,3-oxazolidin-2-one (7 g, 21.52 mmol) as light yellow crystalline solid. 1H NMR (500 MHz, CDCl3) δ7.90 (s, 1H), 7.82 (s, 2H), 5.91 (d, J=8.3 Hz, 1H), 5.2 (m, 3H), 4.7 (m, 1H).

후처리

  1. customthe volatiles were removed
  2. dissolutionThe crude mixture was dissolved in ethyl acetate (150 mL)
  3. washwashed with aqueous Na2CO3 (100 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resultant oil was purified by column chromatography

출처 및 근거

ORD 기록
ord-1a12d2573986423bbc789a0b60421735
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346825B2

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