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

Chemical Properties

White powder

Uses

Different sources of media describe the Uses of 109183-71-3 differently. You can refer to the following data:
1. N-Boc-2-cyclohexyl-L-glycine is used as pharmaceutical intermediate.
2. N-Boc-L-cyclohexylglycine has been used as a reactant for the preparation of a potent hepatitis C protease inhibitor.

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 
• 2935-35-5 (S)-2-phenylglycine 
• 155905-75-2 [(R)-1-(1-Benzenesulfonyl-cyclohexyl)-2-(tetrahydro-pyran-2-yloxy)-ethyl]-carbamic acid tert-butyl ester 
• 116611-45-1 (2R)-2-t-butoxycarbonylamino-3-phenylsulfonyl-1-(2-tetrahydropyranyloxy)propane 
• 107202-39-1 (S)-1-(cyclohexyl-2-hydroxyethyl)crabamic acid tert-butyl ester 
• 54512-75-3 1-bromo-5-chloropentane 

Downstream Products

• 109183-69-9 Boc-Chg-OPfp 
• 440084-20-8 α-(S)-N-Boc-cyclohexylglycine-2-(S)-pyrrolidinecarboxamide 
• 864801-48-9 tert-butyl (S)-(1-cyclohexyl-2-(methoxy(methyl)amino)-2-oxoethyl)carbamate 
• 873676-47-2 (2S,3aR,4S,6aS)-2-(3-Benzyloxy-propyl)-5-((S)-2-tert-butoxycarbonylamino-2-cyclohexyl-acetyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carboxylic acid methyl ester 
• 145963-14-0 Boc-Chg-Asp(OBzl)-1Nal-N(CH₃)2 
• 145963-12-8 Boc-Chg-Asp(OBzl)-1Nal-NH₂ 
• 367258-51-3 methyl (2S,4R)-1-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxoethyl]-4-[3-(phenylmethoxy)propoxy]-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 
• 367259-61-8 methyl (2S,4R)-1-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxoethyl]-4-[(3-hydroxypropyl)thio]-2-pyrrolidinecarboxylate 
• 430433-13-9 3-(3-Allyloxycarbonyloxy-phenyl)-2-((S)-2-tert-butoxycarbonylamino-2-cyclohexyl-acetoxy)-propionic acid benzyl 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 
• 398476-80-7 [(2'-tert-butylsulfamoyl-biphenyl-4-ylcarbamoyl)-cyclohexyl-methyl]-carbamic acid tert-butyl ester 
• 916313-59-2 ((S)-1-Cyclohexyl-3-diazo-2-oxo-propyl)-carbamic acid tert-butyl ester 
• 402958-93-4 (S)-2-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetylamino)-3,3-dimethyl-butyric acid methyl 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).