PATENT CLAIM ANALYSIS

Application Number: 15876464
Application Type: Utility
Filing Date: 2018-01
Publication Date: 2018-05
Patent Classification: ["556", "415000"]

Abstract:
The present teachings relate to a functionalized silyl cyanide and synthetic methods thereof. As an example, the method may include adding a raw material silane and a cyanide source MCN in an organic solvent to produce the functionalized silyl cyanide in the absence of catalyst or in the presence of a metal salt catalyst. The functionalized silyl cyanide may be used in the reactions that classic TMSCN participates in, to synthesize important intermediates (e.g., cyanohydrin, amino alcohols and α-amino nitrile compounds), with improved reactivity and selectivity. The cyanosilyl ether resulted from the nucleophilic addition of functionalized silyl cyanide to aldehyde or ketone may undergo intramolecular reaction under appropriate conditions to transfer the functional groups on silicon onto the other parts of the product linked to silicon. Such a functional group transfer process may increase the synthesis efficiency and atom economy, as well as afford products unobtainable using traditional TMSCN.

Claim (Index 3):
Use of a functionalized silyl cyanide for nucleophilic addition reaction, comprising the steps of: reacting a functionalized silyl cyanide 1a and electrophilic reagent 3 under the catalysis of a catalyst I, to synthesize a compound 4 by nucleophilic addition reaction;\n wherein, the nucleophilic addition reaction comprises racemic nucleophilic addition reaction and asymmetric nucleophilic addition reaction; the compound 4 is in R and/or S configuration; the process of the reaction is as shown in Scheme (II): wherein, FG is selected from F, Cl, Br, I, CHF 2 , CHCl 2 , \u2014CH 2 CH\u2550CR 2 , \u2014CH\u2550CR 2 , and \u2014C\u2261CR; wherein, \u2014CH 2 CH\u2550CR 2 , \u2014CH\u2550CR 2  and \u2014C\u2261CR are functional groups having unsaturated carbon-carbon bond; wherein, R is H, Me; n=1-5; R 2  is selected from C1-C20 alkyl, phenyl, C6-C20 substituted phenyl, naphthyl, C10-C20 substituted naphthyl, furanyl, C4-C10 substituted furanyl, thienyl, C4-C10 substituted thienyl, pyrryl, C4-C10 substituted pyrryl, pyridyl, and C5-C10 substituted pyridyl; Y is selected from O, NBn, NCbz, NTs, NBoc, NPMP, NP(O)Ph 2 , and CHEWG; wherein, EWG \u2550CN, NO 2 , CO 2 R, CONR 2 , wherein, R=Me, Et, Ph, Bn; R 3  is selected from H; C1-C20 alkyl; ester group CO 2 R, wherein, R=Me, Et, i-Pr, t-Bu, Ph, Bn; and amide CONR 2 , wherein, R=Me, Et, CF 3 ; R 5  is H or silyl; when the substrates are not the same, the corresponding products are different; the catalyst I is used for catalyzing the nucleophilic addition reaction of the functionalized silyl cyanide 1a to the electrophilic reagent 3; and the dosage of the catalyst I is 0.001-0.5 equivalent relative to the electrophilic reagent 3; the racemic nucleophilic addition reaction and the asymmetric nucleophilic addition reaction differ in that, the catalysts are not the same, with the other reaction conditions are the same: for the racemic nucleophilic addition reaction, the catalyst I\u2032 comprises: 1) achiral inorganic Lewis base catalyst, comprising: inorganic metal carbonate, carboxylate and phosphate; wherein, the inorganic metal carbonate comprises K 2 CO 3 , Li 2 CO 3 , Na 2 CO 3 , and Cs 2 CO 3 ; the carboxylate comprises KOAc, LiOAc, NaOAc, and CsOAc; and the phosphate comprises K 3 PO 4 , Li 3 PO 4 , and Na 3 PO 4 ; 2) achiral organic Lewis base catalyst, comprising: tertiary amine compounds comprising Et 3 N, DABCO, and i-Pr 2 NEt; piperidine, pyridine derivatives comprising DMAP, N-methyl piperidine, oxynitride 3) achiral Lewis acid catalyst, comprising metal salt comprising ZnI 2 , KI, Zn(OTf) 2 , and TiCl 4 ; for the asymmetric nucleophilic addition reaction, the catalyst I\u2033 comprises: chiral Lewis acid catalyst, chiral Lewis base catalyst and chiral bifunctional catalyst having both Lewis acid functional group and Lewis base functional group co-existing in one molecule, and a variety of catalyst systems formed by combination of chiral catalysts and achiral catalysts, containing the catalysts as shown in the following Formula (IC1)\u02dcFormula (IC6): wherein, in Formula (IC1), R 4  is H, CH 3 , OEt, Ot-Bu; in Formula (IC2), X 1  is OTf, NTf 2 ; in Formula (IC5), n is 1-5.

Metadata:
- Claim Count in Document: 15.0
- Percentile: 86.0
- Lexical Diversity: 1.60396
- Patent Class: 556.0
- Transitional Phrase Type: open
- Component Type: 1
- Foreign Priority: True
- Related Applications: ['14547641', '14547696', '15102968', '15746646', '14609612']

Analysis Scores:
- 35 USC 101 Eligibility (BERT): 0.6811745013791219
- 35 USC 102 Novelty (BERT): 0.5177153704374977
- Combined Prediction Score: 0.6648285882849596
- Mean Citation Score: 257.21133999999995
- Max Citation Score: 276.37405
- Similarity Product: 170.31004976054433

Labels:
- Claim Label 101: 1
- Claim Label 102: 1
- Claim Label 103: 1
- Claim Label 112: 1
- Combined Label: 1
- Label 101 Adjusted: 1

Dataset: test