Dichloromethane → (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[2'-chloro-5'-nitro-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one

HRID 2093160

Reaktionsgleichung

Reaktionsgleichung von HRID 2093160
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3I)[C@H:14]2[CH3:31])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][C:36]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>O.CCO.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCCCCC>[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[C:36]3[CH:37]=[C:38]([N+:41]([O-:43])=[O:42])[CH:39]=[CH:40][C:35]=3[Cl:34])[C@H:14]2[CH3:31])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Komponenten

8

Edukt 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 24901770(2-Chloro-5-nitrophenyl)boronic acidHCID 53363742(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

Produkt 1

HCID 57704847(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[2'-chloro-5'-nitro-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8058HexaneLösungsmittelHCID 86587398Ethanol toluene waterLösungsmittel

Versuchsvorschrift

A mixture of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-iodo -5-(trifluoromethyl)-benzyl]-4-methyl-1,3-oxazolidin-2-one (1.0 g, 1.68 mmol), 2-chloro-5-nitro phenyl boronic acid (0.67 g, 3 3 mmol), tetrakis(triphenylphosphine)palladium (97 mg, 5% mol) and sodium carbonate (0.39 g, 3.68 mmol) in 50 ml of water/EtOH/toluene (1:2:4) was heated to reflux for 4 h. TLC (CH2Cl2:hexane/1:1) showed that the reaction was complete. The solvents were removed. Water (30 ml) was added. The organic was extracted with methylene chloride (3×40 ml). The combined methylene chloride layers were washed with brine, and dried over sodium sulfate. The title compound was obtained after flash column using CH2Cl2:hexane/6:4 as the eluant. 1H NMR (CDCl3, 500 MHz): δ 1:1 mixture of roamers 8.16-8.31 (m, 1H), 8.21(d, J=2.5 Hz, ½H), 8.16(d, J=2.5 Hz, ½H), 7.90 (s, 1H), 7.71-7.78 (m, 5H), 7.42-7.46 (m, 1H), 5.66 (d, J=4.5 Hz, ½H), 5.64 (d, J=4.5 Hz, ½H), 4.93 (d, J=15.5 Hz, ½H), 4.79 (d, J=16 Hz, ½H), 4.03 (d, J=16 Hz, ½H), 3.94 (m, 1H), 3.91 (d, J=15.5 Hz, ½H), 0.70 (d, J=6.5 Hz, 1.5H), 0.64 (d, J=6.5 Hz, 1.5H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. customThe solvents were removed
  4. additionWater (30 ml) was added
  5. extractionThe organic was extracted with methylene chloride (3×40 ml)
  6. washThe combined methylene chloride layers were washed with brine
  7. dry with materialdried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-18f0fe5d9be943e29dfba2054d9f6769
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440702B2

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