(S)-2-((tert-Butoxycarbonyl)amino)-2-cyclopentylacetic acid

Base Information

• Chemical Name: (S)-2-((tert-Butoxycarbonyl)amino)-2-cyclopentylacetic acid
• CAS No.: 109183-72-4
• Molecular Formula: C12H21NO4
• Molecular Weight: 243.303
• Hs Code.: 29225090
• DSSTox Substance ID: DTXSID40427277
• Wikidata: Q72449050
• Mol file: 109183-72-4.mol

Synonyms:109183-72-4;Boc-L-Cyclopentylglycine;(S)-2-((tert-Butoxycarbonyl)amino)-2-cyclopentylacetic acid;(2S)-2-cyclopentyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid;(2S)-2-{[(tert-butoxy)carbonyl]amino}-2-cyclopentylacetic acid;MFCD00671385;(S)-TERT-BUTOXYCARBONYLAMINO-CYCLOPENTYL-ACETIC ACID;SCHEMBL464205;DTXSID40427277;(2S)-[(tert-Butoxycarbonyl)amino](cyclopentyl)ethanoic acid;(S)-2-((tert-Butoxycarbonyl)amino)-2-cyclopentylaceticacid;AKOS015841385;AKOS015920313;CS-W019414;HY-W018628;DS-14990;PD197022;BB 0262060;EN300-1071310;Q-101640;(2S)-[(tert-Butoxycarbonyl)amino](cyclopentyl)acetic acid;N-alpha-t-Butyloxycarbonyl-L-cyclopentylglycine dicyclohexylamine;(2S)-cyclopentyl({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethanoic acid;N-alpha-t-Butyloxycarbonyl-L-cyclopentylglycine (Boc-L-Gly(cPent)-OH)

Chemical Property of (S)-2-((tert-Butoxycarbonyl)amino)-2-cyclopentylacetic acid

Chemical Property:

• Vapor Pressure: 2.74E-07mmHg at 25°C
• Refractive Index: 1.494
• Boiling Point: 393.5 °C at 760 mmHg
• PKA: 4.06±0.10(Predicted)
• Flash Point: 191.8 °C
• PSA: 75.63000
• Density: 1.137 g/cm³
• LogP: 2.54540
• Storage Temp.: -15°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 243.14705815
• Heavy Atom Count: 17
• Complexity: 289

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-2-((tert-Butoxycarbonyl)amino)-2-cyclopentylaceticAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(C1CCCC1)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](C1CCCC1)C(=O)O
• Uses: (S)-2-((tert-Butoxycarbonyl)amino)-2-cyclopentylacetic Acid is used as a reactant in the synthesis of tripeptide ketoacid inhibitors of hepatitis C virus serine protease.

Technology Process of (S)-2-((tert-Butoxycarbonyl)amino)-2-cyclopentylacetic acid

There total 6 articles about (S)-2-((tert-Butoxycarbonyl)amino)-2-cyclopentylacetic 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:

N-(tert-butyloxycarbonyl) azide (1070-19-5) + (S)-2-amino-2-cyclopentylacetic acid (2521-84-8,2521-82-6) → (S)-2-((tert-butoxycarbonyl)amino)-2-cyclopentylacetic acid (109183-72-4)

Guidance literature:

With sodium hydroxide; magnesium oxide; In 1,4-dioxane;

DOI:10.1021/jm00292a001

Reference yield:

(2R)-2-t-butoxycarbonylamino-3-phenylsulfonyl-1-(2-tetrahydropyranyloxy)propane (116611-45-1) → (S)-2-((tert-butoxycarbonyl)amino)-2-cyclopentylacetic acid (109183-72-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) n-BuLi / 1) THF, -78 deg C, 15 min, 2) THF, -78 to 20 deg C then RT, 48 h

2: n-BuLi / tetrahydrofuran / -40 °C

3: 6percent Na-Hg, Na₂HPO₄ / methanol / 3 h / 0 - 20 °C

4: PPTS / ethanol / 6 h / 50 °C

5: CrO₃, H₂SO₄ / 1 h / 0 - 20 °C

With chromium(VI) oxide; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; sulfuric acid; pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; ethanol;

DOI:10.1016/S0040-4039(00)76520-8

Reference yield:

((S)-1-Cyclopentyl-2-hydroxy-ethyl)-carbamic acid tert-butyl ester (732282-67-6) → (S)-2-((tert-butoxycarbonyl)amino)-2-cyclopentylacetic acid (109183-72-4)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; at 0 - 20 ℃; for 1h; Yield given;

DOI:10.1016/S0040-4039(00)76520-8

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

(S)-2-amino-2-cyclopentylacetic acid

((S)-1-Cyclopentyl-2-hydroxy-ethyl)-carbamic acid tert-butyl ester

(2R)-2-t-butoxycarbonylamino-3-phenylsulfonyl-1-(2-tetrahydropyranyloxy)propane

Downstream raw materials:

C₂₄H₃₂N₂O₆

Refernces