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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.

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  • 109183-71-3 Structure
  • Basic information

    1. Product Name: Boc-L-Cyclohexylglycine
    2. 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
    3. CAS NO:109183-71-3
    4. Molecular Formula: C13H23NO4
    5. Molecular Weight: 257.33
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 109183-71-3.mol
  • Chemical Properties

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

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: 24/25
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 109183-71-3(Hazardous Substances Data)

109183-71-3 Usage

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.

Check Digit Verification of cas no

The CAS Registry Mumber 109183-71-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,9,1,8 and 3 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 109183-71:
(8*1)+(7*0)+(6*9)+(5*1)+(4*8)+(3*3)+(2*7)+(1*1)=123
123 % 10 = 3
So 109183-71-3 is a valid CAS Registry Number.
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)

109183-71-3 Well-known Company Product Price

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  • TCI America

  • (B3839)  N-(tert-Butoxycarbonyl)-L-2-cyclohexylglycine  >98.0%(HPLC)

  • 109183-71-3

  • 1g

  • 490.00CNY

  • Detail
  • TCI America

  • (B3839)  N-(tert-Butoxycarbonyl)-L-2-cyclohexylglycine  >98.0%(HPLC)

  • 109183-71-3

  • 5g

  • 1,690.00CNY

  • Detail
  • Alfa Aesar

  • (H62466)  N-Boc-2-cyclohexyl-L-glycine, 97%   

  • 109183-71-3

  • 1g

  • 517.0CNY

  • Detail
  • Alfa Aesar

  • (H62466)  N-Boc-2-cyclohexyl-L-glycine, 97%   

  • 109183-71-3

  • 5g

  • 2327.0CNY

  • Detail
  • Aldrich

  • (15091)  Boc-Chg-OH  ≥98.0% (TLC)

  • 109183-71-3

  • 15091-5G

  • 2,317.77CNY

  • Detail

109183-71-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name (2S)-2-cyclohexyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid

1.2 Other means of identification

Product number -
Other names Boc-L-Cyclohexylglycine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:109183-71-3 SDS

109183-71-3Relevant articles and documents

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

Choi, Jun Yong,Fuerst, Rita,Knapinska, Anna M.,Taylor, Alexander B.,Smith, Lyndsay,Cao, Xiaohang,Hart, P. John,Fields, Gregg B.,Roush, William R.

, p. 5816 - 5825 (2017)

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

SELECTIVE MATRIX METALLOPROTEINASE-13 INHIBITORS

-

Paragraph 00148, (2019/01/06)

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

Duan, Shaobo,Li, Sanliang,Ye, Xinyi,Du, Nuan-Nuan,Tan, Choon-Hong,Jiang, Zhiyong

supporting information, p. 7770 - 7778 (2015/08/18)

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.

Azetidines and spiro azetidines as novel P2 units in hepatitis C virus NS3 protease inhibitors

Bondada, Lavanya,Rondla, Ramu,Pradere, Ugo,Liu, Peng,Li, Chengwei,Bobeck, Drew,McBrayer, Tamara,Tharnish, Philip,Courcambeck, Jerome,Halfon, Philippe,Whitaker, Tony,Amblard, Franck,Coats, Steven J.,Schinazi, Raymond F.

, p. 6325 - 6330 (2013/11/19)

Herein, we report the synthesis and structure-activity relationship studies of new analogs of boceprevir 1 and telaprevir 2. Introduction of azetidine and spiroazetidines as a P2 substituent that replaced the pyrrolidine moiety of 1 and 2 led to the disco

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

Nguyen, Jeffrey-Tri,Kato, Keiko,Kumada, Henri-Obadja,Hidaka, Koushi,Kimura, Tooru,Kiso, Yoshiaki

scheme or table, p. 1832 - 1837 (2011/05/05)

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).

PYRROLO [2, 3 - B] PYRAZINE - 7 - CARBOXAMIDE DERIVATIVES AND THEIR USE AS JAK AND SYK INHIBITORS

-

Page/Page column 136-137, (2011/12/04)

The present invention relates to the use of novel pyrrolopyrazine derivatives of Formula (I), wherein the variables Q and R, R2, and R3 are defined as described herein, which inhibit JAK and SYK and are useful for the treatment of auto-immune and inflammatory diseases.

ARYLGLYCINE DERIVATIVES FOR USE AS GLYCINE TRANSPORT INHIBITORS

-

Page 54, (2010/02/06)

The present invention relates to compounds of Formula (I) and salts solvates and hydrates thereof. The invention further relates to pharmaceutical compositions containing said compounds and methods of treating neurological and neuropsychistric disorders using said compounds.

Exploration of the P1 SAR of aldehyde cathepsin K inhibitors.

Catalano, John G,Deaton, David N,Furfine, Eric S,Hassell, Annie M,McFadyen, Robert B,Miller, Aaron B,Miller, Larry R,Shewchuk, Lisa M,Willard Jr., Derril H,Wright, Lois L

, p. 275 - 278 (2007/10/03)

The synthesis and biological activity of a series of aldehyde inhibitors of cathepsin K are reported. Exploration of the properties of the S(1) subsite with a series of alpha-amino aldehyde derivatives substituted at the P(1) position afforded compounds with cathepsin K IC(50)s between 52 microM and 15 nM.

A Versatile Method for the Synthesis of (S)- or (R)-Cycloalkylglycines, (S)- or (R)-N-Heterocyclic and α,β-Unsaturated N-Heterocyclic α-Amino Acids

Pauly, Regine,Sasaki, N. Andre,Potier, Pierre

, p. 237 - 240 (2007/10/02)

Two different types of cyclic α-amino acids, cycloalkylglycines and N-heterocyclic α-amino acids, were prepared in optically pure form from the same chiral synthon 1-(R) (or 1-(S)) simply by altering the quantity or type of base required for anion formation.Elaboration of the heterocyclic intermediate 3 provided α,β-unsaturated N-heterocyclic α-amino acids.

Heterocyclic inhibitors of farnesyl protein transferase

-

, (2008/06/13)

Inhibition of farnesyl protein transferase is effected by compounds of the formula its enantiomers, diastereomers, pharmaceutically acceptable salts, prodrugs or solvates thereof, wherein:, A1 and A2 are each independently H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, phenyl or substituted phenyl;, G1 is S or O;, G2 is H, -C(O)OH, -C(O)NH2, 5-tetrazolyl, -C(O)N(R7)OH or -CH2OH;, X is O or R8N;, Y and Z are each independently -CH2- or -C(O)-;, R1, R2, R3, R4, R5, R6 and R7 are each independently H or alkyl;, R1 may also be alkanoyl, R1 and A1 taken together may be -(CH2)m;, R8 is H, alkyl, phenyl, phenylalkyl, substituted phenyl, (substituted phenyl)alkyl or -C(O)R9;, R9 is H, alkyl, phenyl, phenylalkyl, substituted phenyl or (substituted phenyl)alkyl;, m is 3 or 4;, n is 0, 1 or 2;, p is 0, 1 or 2; and, q is 0 or 1, with the proviso that when p is 0, then q is also 0.

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