Sodium Hydroxide → HCID 67225632, Verbindung

HRID 1043092Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1043092
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14](=O)[CH3:15])=[CH:4][CH:3]=1.[N:17]1([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.[BH3-]C#N.[Na+].[OH-].[Na+]>ClCCl.CO.[Ti](Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:14]([N:20]2[CH2:19][CH2:18][N:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21]2)[CH3:15])=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 14798Sodium HydroxideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 201001921-(4'-Chloro-[1,1'-biphenyl]-2-yl)ethanone

Produkt 1

HCID 67225632HCID 67225632, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24193Titanium TetrachlorideKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of EXAMPLE 110A (1.9 g) in dichloromethane (3 mL) was treated with 1M titanium(IV) chloride in dichloromethane (9.06 mL), cooled to 0° C., treated with tert-butyl piperazine-1-carboxylate (3.07 g), stirred at ambient temperature for 3 hours, treated with NaCNBH3 (0.828 g) in methanol (5 ml), stirred at room temperature overnight, neutralized with aqueous NaOH and concentrated. The concentrate was treated with ethyl acetate and filtered. The organic filtrate was washed with water and concentrated. The concentrate was dissolved in methanol/trifluoroacetic acid/dimethylsulfoxide, loaded onto a reverse phase C18 column and eluted with 0-80% acetonitrile in 0.1% trifluoroacetic acid water over 70 minutes.

Aufarbeitung

  1. stirringstirred at room temperature overnight
  2. concentrationconcentrated
  3. additionThe concentrate was treated with ethyl acetate
  4. filtrationfiltered
  5. washThe organic filtrate was washed with water
  6. concentrationconcentrated
  7. dissolutionThe concentrate was dissolved in methanol/trifluoroacetic acid/dimethylsulfoxide
  8. washeluted with 0-80% acetonitrile in 0.1% trifluoroacetic acid water over 70 minutes

Quellen und Nachweise

ORD-Eintrag
ord-44ae91ba6fbe4f8ca46ab94a65af50fc
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557983B2

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