(S)-2-(((Benzyloxy)carbonyl)amino)-2-cyclohexylacetic acid

Base Information

• Chemical Name: (S)-2-(((Benzyloxy)carbonyl)amino)-2-cyclohexylacetic acid
• CAS No.: 69901-75-3
• Molecular Formula: C16H21NO4
• Molecular Weight: 291.347
• Hs Code.: 2924299090
• European Community (EC) Number: 478-210-0,615-025-8
• DSSTox Substance ID: DTXSID80585042
• Nikkaji Number: J2.538.208K
• Wikidata: Q72516131
• Mol file: 69901-75-3.mol

Synonyms:69901-75-3;Z-Chg-OH;(S)-2-(((Benzyloxy)carbonyl)amino)-2-cyclohexylacetic acid;Cbz-Cyclohexyl-L-glycine;cbz-l-cyclohexylglycine;(S)-Cbz-Cyclohexylglycine;(2S)-2-cyclohexyl-2-(phenylmethoxycarbonylamino)acetic acid;Z-L-Chg-OH;Z-L-2-cyclohexylglycine;MFCD00191083;SCHEMBL2326093;CBZ-L-CYCLOHEXYL GLYCINE;(s)-2-(benzyloxycarbonylamino)-2-cyclohexylacetic acid;(2S)-{[(Benzyloxy)carbonyl]amino}(cyclohexyl)acetic acid;DTXSID80585042;CS-M2257;HY-I0109;AKOS016842422;AS-15058;PD196175;NS00077873;F14547;M06093;(s)-benzyloxycarbonylamino-cyclohexyl-acetic acid;EN300-6748036;(S)-2-(benzyloxy)carbonyl)amino)-2-cyclohexylacetic acid;(2S)-2-{[(benzyloxy)carbonyl]amino}-2-cyclohexylacetic acid

Chemical Property of (S)-2-(((Benzyloxy)carbonyl)amino)-2-cyclohexylacetic acid

Chemical Property:

• Vapor Pressure: 1.68E-10mmHg at 25°C
• Melting Point: 111-114°C
• Refractive Index: 1.552
• Boiling Point: 492.1 °C at 760 mmHg
• PKA: 3.99±0.10(Predicted)
• Flash Point: 251.4 °C
• PSA: 75.63000
• Density: 1.2 g/cm³
• LogP: 3.33720
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 291.14705815
• Heavy Atom Count: 21
• Complexity: 346

Purity/Quality:

99% ^*data from raw suppliers

Z-L-2-cyclohexylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)C(C(=O)O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1CCC(CC1)[C@@H](C(=O)O)NC(=O)OCC2=CC=CC=C2
• Uses: Cbz-Cyclohexyl-L-glycine is a gylicine derivative used in the preparation of peptides as inhibitors of serine proteases, particularly hepatitis C virus NS3-NS4A protease. A gylicine derivative used in the preparation of peptides as inhibitors of serine proteases, particularly hepatitis C virus NS3-NS4A protease.

Technology Process of (S)-2-(((Benzyloxy)carbonyl)amino)-2-cyclohexylacetic acid

There total 5 articles about (S)-2-(((Benzyloxy)carbonyl)amino)-2-cyclohexylacetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.9%

(2S)-amino(cyclohexyl)ethanoic acid (14328-51-9) + benzyl chloroformate (501-53-1,94274-21-2) → (S)-[[(benzyloxy)carbonyl]amino](cyclohexyl)acetic acid (69901-75-3)

Guidance literature:

(2S)-amino(cyclohexyl)ethanoic acid; benzyl chloroformate; With sodium hydroxide; In water;

With hydrogenchloride; In water; isopropyl alcohol; Product distribution / selectivity;

Reference yield:

N-(benzyloxycarbonyl)-α-dehydrocyclohexylglycine → (S)-[[(benzyloxy)carbonyl]amino](cyclohexyl)acetic acid (69901-75-3) + (R)-N-benzyloxycarbonylcyclohexylglicine (69901-85-5)

Guidance literature:

With (R)-(-)-[(S)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; hydrogen; triethylamine; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; In ethanol; 1,2-dichloro-ethane; at 25 ℃; for 24h; under 4654.33 Torr; Title compound not separated from byproducts;

DOI:10.1021/ol050869s

Reference yield:

O-benzyl carbamate (621-84-1) → (S)-[[(benzyloxy)carbonyl]amino](cyclohexyl)acetic acid (69901-75-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 43 percent / methanesulfonic acid / toluene / 2 h / Heating

2: H₂; (R)-(S)-1-Ph₃P-2-(CHMeP(t-Bu)2)ferrocene; Et₃N / [(p-cymene)RuCl₂]2 / ethanol; 1,2-dichloro-ethane / 24 h / 25 °C / 4654.33 Torr

With methanesulfonic acid; (R)-(-)-[(S)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; hydrogen; triethylamine; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; In ethanol; 1,2-dichloro-ethane; toluene;

DOI:10.1021/ol050869s

upstream raw materials:

O-benzyl carbamate

2-cyclohexyl-2-oxoethanoic acid

(2S)-amino(cyclohexyl)ethanoic acid

benzyl chloroformate

Downstream raw materials:

((S)-1-Cyclohexyl-2-hydroxy-ethyl)-carbamic acid benzyl ester

N-(cyclohexyl(methoxy)methyl)benzyl carbamate

(S)-tert-butyl 2-amino-2-cyclohexylacetate

Refernces

• 1、 Shultz, C. Scott,Dreher, Spencer D.,Ikemoto, Norihiro,Williams, J. Michael,Grabowski, Edward J. J.,Krska, Shane W.,Sun, Yongkui,Dormer, Peter G.,DiMichele, Lisa. "Asymmetric hydrogenation of N-sulfonylated-α-dehydroamino acids: Toward the synthesis of an anthrax lethal factor inhibitor". . p. 3405 - 3408. Retrieved 2007/10/03.