Trimethylsilyl cyanide → HCID 13521702, 화합물

HRID 2121002노트

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HRID 2121002 반응식
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]

참가 물질

9

반응물 4

HCID 82115Trimethylsilyl cyanideHCID 247831D-(2-Chlorophenyl)glycineHCID 13521702HCID 13521702, 화합물HCID 131724342HCID 131724342, 화합물

생성물 2

HCID 13521702HCID 13521702, 화합물HCID 131724341HCID 131724341, 화합물

시약·촉매·용매 3

HCID 11026Titanium isopropoxide촉매HCID 1140Toluene용매HCID 3283Diethyl Ether용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-d828bf5350344ca8979612e41b33de9a
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06693168B1

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