109183-71-3

Basic information

• Product Name: Boc-L-Cyclohexylglycine
• Synonyms: N-ALPHA-BUTOXYCARBONYL-L-CYCLOHEXYLGLYCINE;N-ALPHA-BUTOXYCARBONYL-L-CYCLOHEXYLGLYCINE HYDRATE;N-BOC-2-CYCLOHEXYL-L-GLYCINE;(S)-TERT-BUTOXYCARBONYLAMINO-CYCLOHEXYL-ACETIC ACID;BOC-CHG-OH H2O;BOC-CHG-OH;BOC-CYCLOHEXYL-GLYCINE;BOC-CYCLOHEXYL-GLY-OH
• CAS NO: 109183-71-3
• Molecular Formula: C₁₃H₂₃NO₄
• Molecular Weight: 257.33
• Mol File: 109183-71-3.mol
• Article Data: 13

Chemical Properties

• Melting Point: 83°C(lit.)
• Boiling Point: 407.9 °C at 760 mmHg
• Flash Point: 200.5 °C
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 1.111 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• PKA: 4.01±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 5553687
• CAS DataBase Reference: Boc-L-Cyclohexylglycine(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-L-Cyclohexylglycine(109183-71-3)
• EPA Substance Registry System: Boc-L-Cyclohexylglycine(109183-71-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 109183-71-3(Hazardous Substances Data)

Usage

Description

Boc-L-Cyclohexylglycine, also known as N-Boc-2-cyclohexyl-L-glycine, is a chemical compound that appears as a white powder. It is a derivative of L-Cyclohexylglycine with a Boc (tert-butyloxycarbonyl) protecting group attached to the nitrogen atom. This modification enhances the stability and reactivity of the molecule, making it suitable for various applications in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
Boc-L-Cyclohexylglycine is used as a pharmaceutical intermediate for the synthesis of various drugs and bioactive compounds. Its unique structure and properties allow it to be incorporated into the development of new medications with potential therapeutic benefits.
Used in Hepatitis C Treatment:
Boc-L-Cyclohexylglycine has been utilized as a reactant in the preparation of a potent hepatitis C protease inhibitor. This inhibitor plays a crucial role in the treatment of hepatitis C by targeting and inhibiting the activity of the viral protease enzyme, which is essential for the replication of the virus. By inhibiting this enzyme, the replication of the virus is halted, leading to a reduction in viral load and improvement in the patient's condition.

InChI:InChI=1/C13H23NO4/c1-13(2,3)18-12(17)14(9-11(15)16)10-7-5-4-6-8-10/h10H,4-9H2,1-3H3,(H,15,16)

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 14328-51-9 (2S)-amino(cyclohexyl)ethanoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 107202-39-1 (S)-1-(cyclohexyl-2-hydroxyethyl)crabamic acid tert-butyl ester 
• 54512-75-3 1-bromo-5-chloropentane 
• 116611-45-1 (2R)-2-t-butoxycarbonylamino-3-phenylsulfonyl-1-(2-tetrahydropyranyloxy)propane 
• 155905-75-2 [(R)-1-(1-Benzenesulfonyl-cyclohexyl)-2-(tetrahydro-pyran-2-yloxy)-ethyl]-carbamic acid tert-butyl ester 
• 2935-35-5 (S)-2-phenylglycine 

Downstream Products

• 109183-69-9 Boc-Chg-OPfp 
• 145963-12-8 Boc-Chg-Asp(OBzl)-1Nal-NH₂ 
• 145963-14-0 Boc-Chg-Asp(OBzl)-1Nal-N(CH₃)2 
• 916313-59-2 ((S)-1-Cyclohexyl-3-diazo-2-oxo-propyl)-carbamic acid tert-butyl ester 
• 398476-80-7 [(2'-tert-butylsulfamoyl-biphenyl-4-ylcarbamoyl)-cyclohexyl-methyl]-carbamic acid tert-butyl ester 
• 367259-79-8 (2S,4R)-1-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-4-(3-hydroxy-1,1-dimethyl-propoxy)-pyrrolidine-2-carboxylic acid methyl ester 
• 430433-13-9 3-(3-Allyloxycarbonyloxy-phenyl)-2-((S)-2-tert-butoxycarbonylamino-2-cyclohexyl-acetoxy)-propionic acid benzyl ester 
• 367260-31-9 (S,S)-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester 
• 367259-61-8 methyl (2S,4R)-1-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxoethyl]-4-[(3-hydroxypropyl)thio]-2-pyrrolidinecarboxylate 
• 367259-20-9 methyl (2S,4R)-1-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxoethyl]-4-[(phenylsulfonyl)amino]-2-pyrrolidinecarboxylate 
• 367258-51-3 methyl (2S,4R)-1-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxoethyl]-4-[3-(phenylmethoxy)propoxy]-2-pyrrolidinecarboxylate 
• 440084-20-8 α-(S)-N-Boc-cyclohexylglycine-2-(S)-pyrrolidinecarboxamide 
• 606124-80-5 (1-cyclohexyl-2-oxo-2-piperidin-1-yl-ethyl)-carbamic acid tert-butyl ester 

Relevant articles and documents

Structure-Based Design and Synthesis of Potent and Selective Matrix Metalloproteinase 13 Inhibitors

We describe the use of comparative structural analysis and structure-guided molecular design to develop potent and selective inhibitors (10d and (S)-17b) of matrix metalloproteinase 13 (MMP-13). We applied a three-step process, starting with a comparative

Enantioselective Synthesis of Dialkylated α-Hydroxy Carboxylic Acids through Asymmetric Phase-Transfer Catalysis

In the presence of an L-tert-leucine-derived urea-ammonium salt as phase-transfer catalyst, a highly enantioselective alkylation of 5H-oxazol-4-ones with various benzyl bromides and allylic bromides has been developed to furnish catalytic asymmetric synthesis of biologically important dialkylated α-hydroxy carboxylic acids with a broad scope. This is the first example of an L-amino acid-derived urea-ammonium salt being used as a phase-transfer catalyst with excellent catalytic efficiency.

Maintaining potent HTLV-I protease inhibition without the P3-cap moiety in small tetrapeptidic inhibitors

The human T cell lymphotropic/leukemia virus type 1 (HTLV-I) causes adult T cell lymphoma/leukemia. The virus is also responsible for chronic progressive myelopathy and several inflammatory diseases. To stop the manufacturing of new viral components, in our previous reports, we derived small tetrapeptidic HTLV-I protease inhibitors with an important amide-capping moiety at the P3 residue. In the current study, we removed the P3-cap moiety and, with great difficulty, optimized the P3 residue for HTLV-I protease inhibition potency. We discovered a very potent and small tetrapeptidic HTLV-I protease inhibitor (KNI-10774a, IC50 = 13 nM).