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

HRID 529697ノート

反応式

HRID 529697 の反応式
[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

参加物

5

反応物 3

HCID 3776Isopropanol2 回HCID 10906Tert-Butyl nitriteHCID 86682260(2S)-2-[(S)-[3,5-Bis(trifluoromethyl)phenyl](hydroxy)methyl]but-3-enehydrazide

生成物 1

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

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

反応条件

温度
50 °C

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-1a12d2573986423bbc789a0b60421735
出典データセット
uspto-grants-2016_05
特許番号
US09346825B2

反応ノート

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