172695-22-6

Basic information

• Product Name: 3-N-BOC-(S)-AMINO BUTYRONITRILE
• Synonyms: 3-N-BOC-(S)-AMINO BUTYRONITRILE;Carbamic acid, [(1S)-2-cyano-1-methylethyl]-, 1,1-dimethylethyl ester (9CI);tert-butyl [(1S)-2-cyano-1-Methylethyl]carbaMate;(S)-tert-butyl 1-cyanopropan-2-ylcarbaMate;tert-butyl (S)-(1-cyanopropan-2-yl) carbamate
• CAS NO: 172695-22-6
• Molecular Formula: C₉H₁₆N₂O₂
• Molecular Weight: 184.24
• Product Categories: N-BOC
• Mol File: 172695-22-6.mol

Chemical Properties

• Melting Point: 69-71 °C(Solv: dichloromethane (75-09-2))
• Boiling Point: 309.5°C at 760 mmHg
• Flash Point: 141°C
• Appearance: /
• Density: 1.005g/cm³
• Vapor Pressure: 0.000635mmHg at 25°C
• Refractive Index: 1.447
• Storage Temp.: 2-8°C
• PKA: 11.72±0.46(Predicted)
• CAS DataBase Reference: 3-N-BOC-(S)-AMINO BUTYRONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-N-BOC-(S)-AMINO BUTYRONITRILE(172695-22-6)
• EPA Substance Registry System: 3-N-BOC-(S)-AMINO BUTYRONITRILE(172695-22-6)

Safety Data

• Hazardous Substances Data: 172695-22-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-N-BOC-(S)-AMINO BUTYRONITRILE is used as an intermediate for the synthesis of spermidine analogs of 15-deoxyspergualin, which possess immunosuppressive activities. These analogs have potential applications in the development of novel therapeutics for autoimmune diseases and transplantation medicine, where immunosuppression is a critical factor.
In the synthesis of these analogs, 3-N-BOC-(S)-AMINO BUTYRONITRILE plays a vital role in constructing the core structure of the molecule, which is essential for its biological activity. The compound's reactivity and functional groups allow for further chemical modifications and optimizations, leading to the development of more potent and selective immunosuppressive agents.
Additionally, the compound may also find applications in other areas of drug discovery, such as the synthesis of other bioactive molecules with potential therapeutic benefits. Its unique structure and reactivity make it a valuable tool for medicinal chemists in their quest to develop new and effective treatments for various diseases and conditions.

InChI:InChI=1/C9H16N2O2/c1-7(5-6-10)11-8(12)13-9(2,3)4/h7H,5H2,1-4H3,(H,11,12)/t7-/m0/s1

Upstream product

• 194156-55-3 tert-butyl 1-cyanopropan-2-ylcarbamate 
• 773837-37-9 sodium cyanide 
• 84765-24-2 (S)-O-(p-tolylsulfonyl)-N-(tert-butyloxycarbonyl)-1-hydroxy-2-aminopropane 
• 109208-68-6 Boc-Ala-O-COO-isoBu 
• 15761-38-3 L-N-Boc-Ala 
• 126301-16-4 (2S)-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 79069-13-9 (S)-2-t-butoxycarbonylaminopropan-1-ol 
• 143-33-9 sodium cyanide 
• 13435-20-6 tetraethylammoniumcyanide 
• 161529-20-0 tert-butyl N-[(1S)-2-iodo-1-methylethyl]carbamate 

Downstream Products

• 6078-06-4 (S)-methyl 3-aminobutanoate 
• 106539-14-4 (S)-methyl 3-(tert-butyloxycarbonylamino)butyrate 
• 118173-26-5 (S)-3-tert-butoxycarbonylamino-butanal 
• 170367-79-0 [4-[[3-[[(1,1-dimethylethoxy)carbonyl]amino]butyl](phenylmethyl)amino]butyl]carbamic acid, 11-[[(1,1-dimethylethoxy)carbonyl]amino]-15,15-dimethyl-2,13-dioxo-14-oxa-3,4,12-triaza-11-hexadecen-1-yl ester (S) 
• 252353-89-2 [21-[[(1,1-dimethylethoxy)carbonyl]amino]-1,25,25-trimethyl-10,12,23-trioxo-4-(phenylmethyl)-24-oxa-4,9,13,20,22-pentaaza-21-hexacosen-1-yl]carbamic acid, 1,1-dimethylethyl ester (S) 
• 170367-77-8 2,2,6-trimethyl-4,15-dioxo-9-(phenylmethyl)-3,16-dioxa-5,9,14-triazaoxadecan-18-oic acid (S) 
• 252353-70-1 [3-[[4-(2,4-dioxo-3-oxazolidinyl)butyl](phynylmethyl)amino]-1-methylpropyl]carbamic acid, 1,1-dimethylethyl ester (S) 
• 170367-73-4 3-[(4-aminobutyl)(phenylmethyl)amino-1(S)-methylpropyl]carbamic acid, 1,1-dimethylethyl ester 
• 176982-59-5 3-[(3-cyanopropyl)(phenylmethyl)amino-1(S)-methylpropyl]carbamic acid, 1,1-dimethylethyl ester 
• 176982-58-4 [1(S)-methyl-3-[(phenylmethyl)amino]propyl]carbamic acid, 1,1-dimethylethyl ester 
• 932032-36-5 (S)-N¹²-(tert-butyloxycarbonyl)-N⁹-(o-nitrophenylsulfonyl)-1,12-diamino-4,9-diazatridecane 
• 932032-35-4 (S)-N⁵-(o-nitrophenylsulfonyl)-N⁸-(tert-butyloxycarbonyl)-8-amino-5-aza-1-iodononane 
• 875680-99-2 (S)-N¹-(o-nitrophenylsulfonyl)-N³-(tert-butyloxycarbonyl)-1,3-diaminobutane 
• 176982-57-3 (3-amino-1(S)-methylpropyl)carbamic acid, 1,1-dimethylethyl ester 

Relevant articles and documents

HETEROCYCLIC GLP-1 AGONISTS

This disclosure relates to GLP-1 agonists of Formula (I) : including pharmaceutically acceptable salts and solvates thereof, and pharmaceutical compositions including the same.

Process Optimisation Studies and Aminonitrile Substrate Evaluation of Rhodococcus erythropolis SET1, A Nitrile Hydrolyzing Bacterium

A comprehensive series of optimization studies including pH, solvent and temperature were completed on the nitrile hydrolyzing Rhodococcus erythropolis bacterium SET1 with the substrate 3-hydroxybutyronitrile. These identified temperature of 25 °C and pH of 7 as the best conditions to retain enantioselectivity and activity. The effect of the addition of organic solvents to the biotransformation mixture was also determined. The results of the study suggested that SET1 is suitable for use in selected organo-aqueous media at specific ratios only. The functional group tolerance of the isolate with unprotected and protected β-aminonitriles, structural analogues of β-hydroxynitriles was also investigated with disappointingly poor isolated yields and selectivity obtained. The isolate was further evaluated with the α- aminonitrile phenylglycinonitrile generating acid in excellent yield and ee (>99 % (S) – isomer and 50 % yield). A series of pH studies with this substrate indicated pH 7 to be the optimum pH to avoid product and substrate degradation.

Synthesis and evaluation of chiral β-amino acid-based low-molecular-weight organogelators possessing a methyl/trifluoromethyl side chain

The synthesis and gelation properties of chiral β-amino acid-based low-molecular-weight organogelators, possessing methyl/trifluoromethyl side chains, are reported. The structure of the side chain and chirality were found to be important parameters affecting the gelation ability. The pure enantiomer of the trifluoromethylated β-amino acid displayed good gelation properties due to the formation of fibrillar networks, driven by enhanced amide hydrogen bonding. An investigation of the effects of the alkyl chain length showed that longer alkyl chain improved the gelation ability, yet the same supramolecular structure was observed in all, as well as an odd-even effect in both the melting points and Tg values.

Identification of highly selective and potent orexin receptor 1 antagonists derived from a dual orexin receptor 1/2 antagonist based on the structural framework of pyrazoylethylbenzamide

The design, synthesis, and structure activity relationships of the novel class of pyrazolylethylbenzamide orexin receptor 1-selective antagonists are described. Further derivatization of the prototype dual orexin receptor 1/2 antagonist lead (1) by instal

Synthetic and theoretical investigation on the one-pot halogenation of β-amino alcohols and nucleophilic ring opening of aziridinium ions

Aziridinium ions are useful reactive intermediates for the synthesis of enantiomerically enriched building blocks. However, N,N-dialkyl aziridinium ions are relatively underutilized in the synthesis of optically active molecules as compared to other three

BRANCHED CHAIN ALKYL HETEROAROMATIC RING DERIVATIVE

A branched chain alkyl heteroaromatic ring derivative represented by formula (Ia) or a pharmaceutically acceptable salt thereof is useful for treatment or prophylaxis of diseases such as sleep disorder, depression, anxiety disorder, panic disorder, schizophrenia, drug dependence, Alzheimer's disease, Parkinson's disease, Huntington's disease, eating disorder, cephalalgia, hemicrania, pain, digestive diseases, epilepsy, inflammation, immune-related diseases, endocrine-related diseases and hypertension, on the basis of the orexin (OX) receptor antagonist activity.

A multifaceted secondary structure mimic based on piperidine-piperidinones

Minimalist secondary structure mimics are typically made to resemble one interface in a protein-protein interaction (PPI), and thus perturb it. We recently proposed suitable chemotypes can be matched with interface regions directly, without regard for secondary structures. Here we describe a modular synthesis of a new chemotype 1, simulation of its solution-state conformational ensemble, and correlation of that with ideal secondary structures and real interface regions in PPIs. Scaffold 1 presents amino acid side-chains that are quite separated from each other, in orientations that closely resemble ideal sheet or helical structures, similar non-ideal structures at PPI interfaces, and regions of other PPI interfaces where the mimic conformation does not resemble any secondary structure. 68 different PPIs where conformations of 1 matched well were identified. A new method is also presented to determine the relevance of a minimalist mimic crystal structure to its solution conformations. Thus dld-1-faf crystallized in a conformation that is estimated to be 0.91 kcal-mol-1 above the minimum energy solution state. Do we know, when designing a new peptidomimetic scaffold like the one shown, how it can resemble secondary structures? Design and modular synthesis of this elongated mimic is reported, and the structure is related to ideal and real structures at PPI interfaces.

Entropy-controlled catalytic asymmetric 1,4-type Friedel-crafts reaction of phenols using conformationally flexible guanidine/bisthiourea organocatalyst

Soft and weak cooperation: Conformationally flexible organic compounds were found to promote the title transformation. These "soft" organocatalysts, which are able to control processes through the differential activation entropies (ΔΔS*S-R) of

Synthesis of novel N-protected β3-amino nitriles: study of their hydrolysis involving a nitrilase-catalyzed step

Several commercially available nitrilases were investigated with regard to their potential to hydrolyze N-protected β3-amino nitriles into their corresponding N-protected β3-amino acids. The biotransformations were obtained in different proportions depending on the nitrilase involved. The best hydrolysis results were achieved for the N-Cbz-β3-amino nitrile from l-alanine using the NIT-107, in a phosphate buffer at 0.05 M. However, no biotransformation into the corresponding acids was observed for the N-sulfonylamide β3-amino nitriles. Two simple and efficient procedures to prepare the β3-amino nitriles from their analogous α-amino acids are described. Thirty four new substances were synthesized and characterized over the course of this work.

POLYCYCLIC CARBAMOYLPYRIDONE DERIVATIVE HAVING HIV INTEGRASE INHIBITORY ACTIVITY

The present invention is to provide a novel compound (I), having the anti-virus activity, particularly the HIV integrase inhibitory activity, and a drug containing the same, particularly an anti-HIV drug, as well as a process and an intermediate thereof. Compound (I) wherein Z1 is NR4; R1 is hydrogen or lower alkyl; X is a single bond, a hetero atom group selected from O, S, SO, SO2 and NH, or lower alkylene or lower alkenylene in which the hetero atom group may intervene; R2 is optionally substituted aryl; R3 is hydrogen, a halogen, hydroxy, optionally substituted lower alkyl etc; and R4 and Z2 part taken together forms a ring, to form a polycyclic compound, including e.g., a tricyclic or tetracyclic compound.