Isopropanol → cis-5-[3,5-Bis(trifluoromethyl)phenyl]-4-ethenyl-1,3-oxazolidin-2-one
Reaction equation
[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]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
(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).
Workup
- customthe volatiles were removed
- dissolutionThe crude mixture was dissolved in ethyl acetate (150 mL)
- washwashed with aqueous Na2CO3 (100 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe resultant oil was purified by column chromatography
Sources & evidence
- ORD record
- ord-1a12d2573986423bbc789a0b60421735
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346825B2
Reaction notes
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