Ammonium Chloride → Methyl [3,5-bis(trifluoromethyl)benzyl]{[5'-(1-hydroxyethyl)-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

HRID 217531

Reaktionsgleichung

Reaktionsgleichung von HRID 217531
[CH3:1][Mg]Br.[F:4][C:5]([F:44])([F:43])[C:6]1[CH:7]=[C:8]([CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=1)[CH2:9][N:10]([CH2:15][C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=1[C:26]1[CH:31]=[C:30]([CH:32]=[O:33])[CH:29]=[CH:28][C:27]=1[O:34][CH3:35])[C:11](=[O:14])[O:12][CH3:13].[Cl-].[NH4+]>O1CCCC1>[F:4][C:5]([F:43])([F:44])[C:6]1[CH:7]=[C:8]([CH:36]=[C:37]([C:39]([F:40])([F:42])[F:41])[CH:38]=1)[CH2:9][N:10]([CH2:15][C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=1[C:26]1[CH:31]=[C:30]([CH:32]([OH:33])[CH3:1])[CH:29]=[CH:28][C:27]=1[O:34][CH3:35])[C:11](=[O:14])[O:12][CH3:13]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 11699919Methyl [3,5-bis(trifluoromethyl)benzyl]{[5'-formyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamateHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 11599738Methyl [3,5-bis(trifluoromethyl)benzyl]{[5'-(1-hydroxyethyl)-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methylmagnesium bromide (0.59 mL, 0.83 mmol) was added dropwise to a solution of methyl [3,5-bis(trifluoromethyl)benzyl]{[5′-formyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate (Example 73, 289 mg, 0.49 mmol) in anhydrous tetrahydrofuran at 0° C. The solution was allowed to warm to room temperature. Once the reaction was complete, saturated ammonium chloride solution was added to quench the reaction. The mixture was extracted with methylene chloride, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The title compound was obtained by flash chromatography using 30% acetone/hexane. 1HNMR (CDCl3, 600 MHz) δ 7.73 (s, 1H), 7.58 (m, 1H), 7.32-7.51 (m, 5H), 7.11 (m, 1H), 6.94 (m, 1H), 4.87 (m, 1H), 4.25-4.43 (m, 4H), 3.69 (m, 6H), 1.48 (d, J=4.2 Hz, 3H). LC-MS (M+Na) 632.0 (4.18 min).

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with methylene chloride
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-eba9f37249e44d89912666cc5f3a42cd
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193365B2

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