159991-23-8

Basic information

• Product Name: (R)-N-BOC-3-AMINOBUTYRIC ACID
• Synonyms: BOC-D-BETA-HOMOALANINE;BOC-D-B-HOMOALA-OH;BOC PROTECTED (R)-B-AMINOBUTYRIC ACID;3-N-BOC-3-(R)-AMINO BUTYRIC ACID;(R)-N-BOC-3-AMINOBUTYRIC ACID;(R)-N-(TERT-BUTOXYCARBONYL)-3-AMINOBUTYRIC ACID;(R)-BOC-B2-HOALA-OH;(R)-BOC-BETA2-HAL-OH
• CAS NO: 159991-23-8
• Molecular Formula: C₉H₁₇NO₄
• Molecular Weight: 203.24
• Product Categories: N-BOC;Beta amino acids;pharmacetical;Amino Acid
• Mol File: 159991-23-8.mol
• Article Data: 31

Chemical Properties

• Melting Point: 104-107 °C
• Boiling Point: 339.5 °C at 760 mmHg
• Flash Point: 159.1 °C
• Appearance: /
• Density: 1.101 g/cm³
• Vapor Pressure: 1.69E-05mmHg at 25°C
• Refractive Index: 1.46
• Storage Temp.: Store at 0-5°C
• PKA: 4.43±0.10(Predicted)
• CAS DataBase Reference: (R)-N-BOC-3-AMINOBUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N-BOC-3-AMINOBUTYRIC ACID(159991-23-8)
• EPA Substance Registry System: (R)-N-BOC-3-AMINOBUTYRIC ACID(159991-23-8)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• Hazardous Substances Data: 159991-23-8(Hazardous Substances Data)

Usage

Chemical Properties

Off-white powder

Uses

(R)-3-(tert-Butoxycarbonylamino)butanoic Acid is a non-proteinogenic amino acid that can be used to synthesize peptide analogs.

InChI:InChI=1/C9H17NO4/c1-6(5-7(11)12)10-8(13)14-9(2,3)4/h6H,5H2,1-4H3,(H,10,13)(H,11,12)/t6-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 58610-42-7 (R)-3-aminobutanoic acid hydrochloride 
• 3744-87-4 Boc-(R)-Ala 
• 186581-53-3 diazomethane 
• 3775-73-3 (R)-3-aminobutanoic acid 
• 34619-03-9 tert-butyldicarbonate 
• 43080-09-7 3-t-butoxycarbonylaminobutyric acid 
• 170367-68-7 (2-cyano-1(R)-methylethyl)carbamic acid, 1,1-dimethylethyl ester 
• 28267-25-6 (RS)-2-(aminomethyl)propanoic acid hydrochloride 
• 869468-34-8 (+)-(4R)-4-[(tert-butoxycarbonyl)amino]pentan-2-one 
• 159877-47-1 methyl 3-(R)-[N-(tert-butoxycarbonyl)amino]-propanoate 
• 186521-98-2 N-[(1R)-3-diazo-1-methyl-2-oxopropyl]carbamic acid tert-butyl ester 

Downstream Products

• 934525-68-5 C₁₈H₂₈N₂O₃ 
• 497861-77-5 (+)-tert-butyl [(R)-1-methyl-3-oxopropyl]carbamate 
• 167216-17-3 (-)-tert-butyl [(R)-3-hydroxy-1-methylpropyl]carbamate 
• 163188-28-1 benzyl N-Boc-(3R)-aminobutanoate 
• 193635-07-3 tert-butyl (S)-(4-oxopentan-2-yl)carbamate 
• 159877-49-3 (R)-3-[[(1,1-dimethylethoxy)carbonyl]amino]butanethioamide 
• 220760-44-1 (S)-2-((R)-3-tert-Butoxycarbonylamino-butyrylamino)-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-2-(3-chloro-4-methoxy-phenyl)-1-(2,2,2-trichloro-ethoxycarbonyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester 
• 193071-09-9 (S)-2-((R)-3-tert-Butoxycarbonylamino-butyryloxy)-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-2-(3-chloro-4-methoxy-phenyl)-1-(2,2,2-trichloro-ethoxycarbonyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester 
• 918964-82-6 3-(3-tert-butoxycarbonylamino-butyrylamino)-4-phenyl-butyric acid 4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyl)-benzyl ester 
• 918964-88-2 3-(3-tert-butoxycarbonylamino-butyrylamino)-4-phenyl-butyric acid benzyl ester 
• 159877-48-2 (R)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]butanamide 

Relevant articles and documents

Synthesis and biological activity evaluation of azacycloheptane sulfonamide derivatives as potential orexin receptor antagonists

As the orexin signaling system is crucial for the regulation of the sleep/wake cycle, inhibitors of orexin-1 and orexin-2 receptors are of significant interest in the treatment of insomnia. Herein, a series of novel azacycloheptane sulfonamide derivatives were designed and synthesized, and all the compounds were evaluated as potential orexin receptor inhibitors by FLIPR Tetra calcium assay. A majority of the tested azacycloheptane sulfonamide derivatives showed OX1R and OX2R inhibitory activity. Chloro-substituted derivatives functionalized at the C5 or C6 position of the benzoxazole group exhibited better inhibitory activity for OX1R and OX2R than unsubstituted derivatives functionalized at C5 or C6. In addition, phenyl group modification had positive effects on the inhibitory activities, and an electron-withdrawing fluorine group at the ortho or meta position of the phenyl ring improved the OX2R inhibitory activity of the derivatives. This suggests that azacycloheptane sulfonamide derivatives are promising scaffolds for the development of OX1R and OX2R antagonists.

Preparation method for R-3-aminobutanol

The invention relates to a preparation method for R-3-aminobutanol. The preparation method specifically comprises the following steps: (a) reacting R-3-aminobutyric acid with di-tert-butyl carbonate in the presence of a polar solvent so as to form N-Boc-(R)-3-aminobutyric acid; (b) reducing N-Boc-(R)-3-aminobutyric acid in the presence of a reducing agent and Lewis acid so as to form N-Boc-(R)-3-aminobutanol; and (c) subjecting N-Boc-(R)-3-aminobutanol to a Boc removal in the presence of an acid solvent so as to form R-3-aminobutanol. The preparation method of the invention is simple in process, low in cost, friendly to environment, easier for industrial production and worth promotion.

Facile synthesis of suvorexant, an orexin receptor antagonist, via a chiral diazepane intermediate

A facile synthesis of suvorexant, an orexin receptor antagonist, is described. The key intermediate 6 was prepared from R-3-aminobutyric acid through protection, condensation, deprotection, cyclization, and hydrogenation steps. The title product was obtained with a total yield of 31% (>99% ee) after eight linear steps using commercially available raw materials.