150935-37-8

Basic information

• Product Name: (3R)-3-(N-Boc-amino)-1-chloro-4-phenyl-2-butanone
• Synonyms: (3R)-3-(N-Boc-amino)-1-chloro-4-phenyl-2-butanone;Boc-D-Phe chloromethyl ketone;(R)-tert-Butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate
• CAS NO: 150935-37-8
• Molecular Formula: C₁₅H₂₀ClNO₃
• Molecular Weight: 331.8
• Mol File: 150935-37-8.mol

Chemical Properties

• Appearance: /
• Refractive Index: 1.517
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (3R)-3-(N-Boc-amino)-1-chloro-4-phenyl-2-butanone(CAS DataBase Reference)
• NIST Chemistry Reference: (3R)-3-(N-Boc-amino)-1-chloro-4-phenyl-2-butanone(150935-37-8)
• EPA Substance Registry System: (3R)-3-(N-Boc-amino)-1-chloro-4-phenyl-2-butanone(150935-37-8)

Safety Data

• Hazardous Substances Data: 150935-37-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(3R)-3-(N-Boc-amino)-1-chloro-4-phenyl-2-butanone is used as an intermediate in the synthesis of various pharmaceutical drugs. Its Boc-protected amino group and chloro substituent make it a valuable component in the development of new medications.
Used in Organic Chemistry:
In the field of organic chemistry, (3R)-3-(N-Boc-amino)-1-chloro-4-phenyl-2-butanone serves as a versatile building block for the synthesis of complex organic molecules. Its unique structure allows for further functionalization and modification, enabling the creation of a wide range of compounds with diverse applications.
Used in Research and Development:
(3R)-3-(N-Boc-amino)-1-chloro-4-phenyl-2-butanone is also utilized in research and development settings, where its unique properties can be explored for potential applications in various industries. Its chiral nature and functional groups make it an interesting subject for studies in asymmetric synthesis and other advanced chemical processes.
It is important to handle (3R)-3-(N-Boc-amino)-1-chloro-4-phenyl-2-butanone with care, as the presence of a chloro group can pose hazards if mishandled. Proper safety measures should be taken during its synthesis, storage, and use to ensure the safety of researchers and the environment.

InChI:InChI=1/C15H20ClNO3/c1-15(2,3)20-14(19)17-12(13(18)10-16)9-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,17,19)/t12-/m1/s1

Upstream product

• 19901-50-9 methyl (2R)-2-(t-butoxycarbonylamino)-3-phenylpropionate 
• 79-11-8 chloroacetic acid 
• 21685-51-8 D-phenylalanine methyl ester 
• 673-06-3 D-(R)-phenylalanine 
• 923601-68-7 (R)-dimethylsulfoxonium 2-oxo-3-(tert-butoxycarbonylamino)-4-phenylbutylide 
• 60398-40-5 C₉H₁₁NO₂C₅H₈O₂CO₂C₄H₈ 
• 18942-49-9 Boc-D-Phe-OH 
• 115313-19-4 1-diazo-3(R)-<<(1,1-dimethylethoxy)carbonyl>amino>-4-phenyl-2-butanone 

Downstream Products

• 923601-69-8 (1R,2S)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester 
• 1402142-63-5 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (2R,3S)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl carbamate 
• 406953-32-0 methyl (R)-5-(tert-butoxycarbonylamino)-2-methoxycarbonyl-6-phenyl-2-[2'-(2''-pyridinyl)ethyl]-4-oxohexanoate 
• 161302-38-1 <(R,S)-3-<<(R,S)-3-<<(1,1-dimethylethoxy)carbonyl>amino>-2-hydroxy-4-phenylbutyl>amino>-2-hydroxy-1-(phenylmethyl)propyl>carbamic acid 1,1-dimethylethyl ester 
• 161302-38-1 <(R,R)-3-<<(R,S)-3-<<(1,1-dimethylethoxy)carbonyl>amino>-2-hydroxy-4-phenylbutyl>amino>-2-hydroxy-1-(phenylmethyl)propyl>carbamic acid 1,1-dimethylethyl ester 
• 161302-38-1 (1S-(1R*,2R)(3S*))-<3-<<3-<<(1,1-dimethylethoxy)carbonyl>amino>-2-hydroxy-4-phenylbutyl>amino>-2-hydroxy-1-(phenylmethyl)propyl>carbamic acid 1,1-dimethylethyl ester 

Relevant articles and documents

First stereoselective total synthesis of (3R, 3aS, 6aR)-hexahydrofuro[2,3- b]furan-3-yl (2R,3S)-4-(4-amino-N-isobutyl phenylsulfonamido)-3-hydroxy-1- phenylbutan-2-yl-carbamate (diastereomer of Darunavir)

The stereoselective novel synthesis of (3R,3aS,6aR)-hexahydrofuro [2,3-b]furan-3-yl (2R,3S)-4-(4-amino-N-isobutyl phenyl sulfonamido)-3-hydroxy-1- phenylbutan-2-yl-carbamate, has been accomplished in situ from the intermediate 4- amino-N-((2S,3R)-3-amino-

BISFURANYL PROTEASE INHIBITORS

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1-AMINO LINKED COMPOUNDS

The present invention is directed to compounds of formula (I): or a pharmaceutically acceptable salt thereof; wherein A is (II); X is selected from CH, CF and N, R8 is selected from H, C1-C6 alkyl, aryl, heteroaryl, C1-C6 alkylaryl, C1-C6 alkylheteroaryl, C2-C6 alkyl-O- C1-C6 alkyl, C1-C6 haloalkyl, hydroxy C2-C6 alkyl, -C(O)R9 and -SO2R9, or R7 and R8 combine to form (III), (IV); W is selected from CRlO and CR15, RlO is selected from H, halo, -C(O)NR13R14, C1-C6 alkyl, aryl, heteroaryl, C1-C6 alkylaryl, C1-C6 alkylheteroaryl, C1-C6 alkyl-O- C1-C6 alkyl and hydroxy C1-C6 alkyl; Het is a N-linked 5-membered heteroaryl ring optionally substituted with 1-3 substituents selected from methoxy, Cl, F, CH3, CF3, aryl, heteroaryl, C1-C4 alkylaryl or C1-C4 alkylheteroaryl, for use as inhibitors of the DPP-IV enzyme in the treatment or prevention of conditions including Type II diabetes.

Melanocortin receptor ligands

Disclosed are MC-4 and/or MC-3 receptor ligands, the ligands having a structure according to Formula (I): wherein R2, R4, R4′, R5, R6, R6′, R7, R8, R8′, R9, R9′, R10, Ar, Z1, Z2, Z3, X, B, D, p, q, r and s are as described in the specification and claims, and optical isomers, diastereomers or enantiomers thereof; pharmaceutically-acceptable salts, hydrates, and biohydrolyzable esters, amides or imides thereof. Also disclosed are pharmaceutical compositions comprising the ligands of Formula (I), as well as methods of treating diseases mediate by the MC-4/MC-3 receptors, as described in the Detailed Descriptions section of the specification.

Process for the reduction of carbonyl compounds

PCT No. PCT/JP97/00189 Sec. 371 Date Dec. 29, 1997 Sec. 102(e) Date Dec. 29, 1997 PCT Filed Jan. 29, 1997 PCT Pub. No. WO97/28105 PCT Pub. Date Aug. 7, 1997The present invention provides a process for reducing carbonyl compounds to hydroxy compounds, in particular stereoselectively reducing alpha -aminohaloketone derivatives, under mild conditions in an easy and simple manner, which comprises reacting a carbonyl compound of the general formula (1) with an organoaluminum compound of the general formula (4) to provide the corresponding alcohol compound of the general formula (5).

Aminodiol HIV Protease Inhibitors. 1. Design, Synthesis, and Preliminary SAR

A series of HIV protease inhibitors containing a novel C2 symmetrical "aminodiol" core structure were prepared from amino acid starting materials.The ability of the aminodiols to inhibit HIV replication in cell culture is comparable to their ability to inhibit the isolated enzyme, a result compatible with good cell membrane penetration by this class of compounds.Optimization of the structure-activity in this series led to aminodiol 9a (Ki = 100 nM; ED50(HIV-1) = 80 nM) containing P1/P1' benzyl and P2/P2' Boc substituents.Compound 9a is a selective inhibito r of HIV protease versus other aspartyl proteases such as human renin, human cathepsin D, and porcine pepsin.In addition, 9a is equipotent against HIV-1 and HIV-2 in cell culture and demonstrates similar activity in infected T-lymphocytes and PBMCs.After iv and oral administration in rats, 9a displayed significant oral bioavailability (ca. 40percent) and a promising plasma elimination half-life (4 h).