Trimethylsilyl cyanide → HCID 13521702, Verbindung

HRID 2121002Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2121002
ClC1C=CC=CC=1[NH:8][CH2:9][C:10]([OH:12])=[O:11].[Cl:13][C:14]1[CH:36]=[CH:35][CH:34]=[CH:33][C:15]=1[CH:16]([NH:19][CH:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:17]#[N:18].[Cl:37][C:38]1[CH:45]=[C:44]([Cl:46])[CH:43]=[C:40]([CH:41]=[O:42])[C:39]=1[OH:47].[NH2:48][C@H:49]([C:54]([OH:56])=[O:55])[C:50]([CH3:53])([CH3:52])[CH3:51].[C:57]([O:61][C@H:62]([CH3:68])[C@@H:63]([C:65]([OH:67])=[O:66])[NH2:64])([CH3:60])([CH3:59])[CH3:58].NCC(O)=O.C[Si](C#N)(C)C>C1(C)C=CC=CC=1.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].CCOCC>[Cl:37][C:38]1[CH:45]=[C:44]([Cl:46])[CH:43]=[C:40]([CH:41]=[O:42])[C:39]=1[OH:47].[NH2:48][C@H:49]([C:54]([OH:56])=[O:55])[C:50]([CH3:53])([CH3:52])[CH3:51].[C:57]([O:61][C@H:62]([CH3:68])[C@@H:63]([C:65]([OH:67])=[O:66])[NH2:64])([CH3:60])([CH3:58])[CH3:59].[CH3:14][O:12][C:10](=[O:11])[CH2:9][NH2:8].[Cl:13][C:14]1[CH:36]=[CH:35][CH:34]=[CH:33][C:15]=1[CH:16]([NH:19][CH:20]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:17]#[N:18]

Komponenten

9

Edukt 4

HCID 82115Trimethylsilyl cyanideHCID 247831D-(2-Chlorophenyl)glycineHCID 13521702HCID 13521702, VerbindungHCID 131724342HCID 131724342, Verbindung

Produkt 2

HCID 13521702HCID 13521702, VerbindungHCID 131724341HCID 131724341, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11026Titanium isopropoxideKatalysatorHCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

The following is an example of a solution phase catalyzed reaction to synthesize 2-chlorophenyl glycine. Screening of the above library determined that a preferred catalyst for the formation of N-(2-chloro-a-cyanobenzyl)benzhydrylamine was 3,5-Dichlorosalicylaldehyde-tert-Leucine-(O-tert-Butyl)Threonine-Glycine. 3,5-Dichlorosalicylaldehyde-tert-Leucine-(O-tert-Butyl)Threonine-Glycine methyl ester was synthesized using standard solid-phase synthesis techniques and was added (53.3 mg, 0.1 mmol) under a nitrogen atmosphere to a solution of titanium tetraisopropoxide (29.5 ul, 0.1 mmol) in toluene (2 ml), and the mixture was stirred for about 15 minutes. Ortho-chlorobenzylidenylbenzhydrylamine (306 mg, 1.0 mmol) was added and the mixture stirred until complete dissolution of the substrate (ca. 10 minutes). Trimethylsilylcyanide (267 ul, 2.0 mmol) was added to the solution and the resultant mixture was stirred for 48 hours. Addition of ether (2 ml, 5% water) followed by filtration through silica afforded a product that was predominantly the desired isomer contaminated with a small amount of starting material. Addition of hexanes to the ethereal solution afforded pure N-(2-chloro-a-cyanobenzyl)benzhydrylamine as white crystals. Analysis by HPLC indicated optical purity of >99%.

Aufarbeitung

  1. customreaction
  2. customsolid-phase synthesis techniques
  3. additionOrtho-chlorobenzylidenylbenzhydrylamine (306 mg, 1.0 mmol) was added
  4. stirringthe mixture stirred until complete dissolution of the substrate (ca. 10 minutes)
  5. filtrationfollowed by filtration through silica
  6. customafforded a product that

Quellen und Nachweise

ORD-Eintrag
ord-d828bf5350344ca8979612e41b33de9a
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06693168B1

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