Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (2S)-2-{[1-(4-bromophenyl)-2-methylprop-2-enyl]oxy}-N-(cyanomethyl)-4-methylpentanamide

HRID 1180414Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1180414
ClC(Cl)(Cl)C(=N)O[CH:5]([C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=1)[C:6]([CH3:8])=[CH2:7].[C:19]([CH2:21][NH:22][C:23](=[O:30])[C@@H:24]([OH:29])[CH2:25][CH:26]([CH3:28])[CH3:27])#[N:20].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.CC(C)=O.CCOC(C)=O>C(Cl)Cl.CCOC(C)=O>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([CH:5]([O:29][C@@H:24]([CH2:25][CH:26]([CH3:27])[CH3:28])[C:23]([NH:22][CH2:21][C:19]#[N:20])=[O:30])[C:6]([CH3:8])=[CH2:7])=[CH:10][CH:11]=1

Komponenten

7

Edukt 4

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 21584569Ethylacetate acetoneHCID 694696351-(4-Bromophenyl)-2-methylprop-2-enyl 2,2,2-trichloroethanimidoateHCID 86605382HCID 86605382, Verbindung

Produkt 1

HCID 10045254(2S)-2-{[1-(4-bromophenyl)-2-methylprop-2-enyl]oxy}-N-(cyanomethyl)-4-methylpentanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-bromophenyl)-2-methylprop-2-enyl 2,2,2-trichloroethanimidoate of step 2 (0.81 mmol, 300 mg) in CH2Cl2 (6 mL) was added (2S)-N-(cyanomethyl)-2-hydroxy-4-methylpentanamide from Step 1, Example 67 (0.81 mmol, 137 mg) and then PPTS (0.081 mmol, 20 mg). The mixture was stirred at r.t. for 72 h. The mixture was diluted with EtOAc and washed with NaHCO3. The organic extract was dried (anhyd. MgSO4) and concentrated under reduced pressure to give an oil. Chromatography (10% Acetone/EtOAc) gave 2 diastereomers (20 mg each).

Aufarbeitung

  1. washwashed with NaHCO3
  2. extractionThe organic extract
  3. dry with materialwas dried (anhyd. MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customto give an oil

Quellen und Nachweise

ORD-Eintrag
ord-2fcf829d65cf462cabf88461e84d00fe
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279478B2

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