(1S,2R)-2-(Boc-amino)cyclopentanecarboxylic Acid

Base Information

• Chemical Name: (1S,2R)-2-(Boc-amino)cyclopentanecarboxylic Acid
• CAS No.: 136315-70-3
• Molecular Formula: C11H19NO4
• Molecular Weight: 229.276
• Hs Code.: 29242990
• European Community (EC) Number: 812-189-4,853-832-9
• DSSTox Substance ID: DTXSID00361461
• Mol file: 136315-70-3.mol

Synonyms:137170-89-9;(1S,2R)-2-(Boc-amino)cyclopentanecarboxylic Acid;(1S,2R)-2-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid;(1S,2R)-Boc-2-amino-1-cyclopentanecarboxylic acid;(1S,2R)-2-{[(tert-butoxy)carbonyl]amino}cyclopentane-1-carboxylic acid;(1S,2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylic acid;MFCD09750528;(1S,2R)-2-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid;(1S,2R)-2-tert-Butoxycarbonylamino-cyclopentanecarboxylic acid;(1S,2R)-2-((tert-butoxycarbonyl)amino)cyclopentane-1-carboxylic acid;(1S,2R)-2-[(tert-butoxycarbonyl)amino]cyclopentane-1-carboxylic acid;(1S,2R)-2-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylic acid;(1S,2R)-2-Boc-amino-cyclopentanecarboxylic acid;SCHEMBL2493768;DTXSID00361461;245115-25-7;AMY19368;AKOS016843423;TS-7115;CS-0037061;EN300-255718;EN300-7161831;A886548;J-500288;Z2306763839;rac-(1R,2S)-2-{[(tert-butoxy)carbonyl]amino}cyclopentane-1-carboxylic acid;Cyclopentanecarboxylic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, (1S,2R)-

Chemical Property of (1S,2R)-2-(Boc-amino)cyclopentanecarboxylic Acid

Chemical Property:

• Vapor Pressure: 6.55E-07mmHg at 25°C
• Melting Point: 90-94 °C
• Refractive Index: 1.495
• Boiling Point: 382.5 °C at 760 mmHg
• PKA: 4.53±0.40(Predicted)
• Flash Point: 185.1 °C
• PSA: 75.63000
• Density: 1.15 g/cm³
• LogP: 2.15530
• Storage Temp.: 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 229.13140809
• Heavy Atom Count: 16
• Complexity: 282

Purity/Quality:

99% ^*data from raw suppliers

cis-2-(tert-Butoxycarbonylamino)-1-cyclopentanecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1CCCC1C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H]1CCC[C@@H]1C(=O)O
• Uses: cis-2-(tert-Butoxycarbonylamino)-1-cyclopentanecarboxylic acid is carboxylic acid derivatives and can be used as a pharmaceutical intermediate.

Technology Process of (1S,2R)-2-(Boc-amino)cyclopentanecarboxylic Acid

There total 28 articles about (1S,2R)-2-(Boc-amino)cyclopentanecarboxylic 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: 84.0%

(1R*,2S*)-1-(tert-butoxycarbonylamino)-2-hydroxymethylcyclopentane → (±)-cis-2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylic acid (136315-70-3)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; water; In acetone; at 0 ℃; for 0.833333h;

DOI:10.1248/cpb.41.1012

Reference yield: 60.0%

di-tert-butyl dicarbonate (24424-99-5) + (1RS,2SR)-cispentacin (57043-00-2,37910-65-9) → (±)-cis-2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylic acid (136315-70-3)

Guidance literature:

(1RS,2SR)-cispentacin; With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; for 0.5h; Inert atmosphere;

di-tert-butyl dicarbonate; In tetrahydrofuran; water; for 4h; Inert atmosphere;

DOI:10.1002/anie.201800169

Reference yield:

hex-5-en-1-al (764-59-0) → (±)-cis-2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylic acid (136315-70-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 76 percent / CH₂Cl₂ / 2.5 h / 20 °C

2.1: AIBN / benzene / 4 h / Heating

3.1: H₂; (+/-)-10-camphorsulfonic acid / Pd(OH)2/C / methanol / 19.5 h / 20 °C

4.1: 239 mg / Et₃N / CH₂Cl₂ / 5 h / 20 °C

5.1: 99 percent / mCPBA / CH₂Cl₂ / 4.5 h / 0 °C

6.1: 76 percent / AcONa / various solvent(s) / 3 h / Heating

7.1: 9-BBN / tetrahydrofuran; hexane / 8 h / 20 °C

7.2: 55 percent / H₂O₂; NaOH / tetrahydrofuran; hexane; H₂O / 16 h / 20 °C

8.1: NaIO₄; RuO₂*H₂O / H₂O; acetone / 7 h / 20 °C

With ruthenium(IV) oxide; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; hydrogen; sodium acetate; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetone; benzene;

DOI:10.1016/S0040-4020(02)00412-X

upstream raw materials:

5-Hexen-1-ol

hex-5-en-1-al

methyl 5-hexenoate

di-tert-butyl dicarbonate

Downstream raw materials:

(-)-N-(tert-butyloxycarbonyl)-cis-2-aminocyclopentanecarboxylic acid

(1S,2R)-2-((tert-butoxycarbonyl)amino)cyyclopentane-1-carboxylic acid

C₆H₁₂N₂O*(x)ClH

Refernces

• 1、 Miyata, Okiko,Muroya, Kanami,Kobayashi, Tomoko,Yamanaka, Rina,Kajisa, Seiko,Koide, Junko,Naito, Takeaki. "Radical cyclization in heterocycle synthesis. Part 13: Sulfanyl radical addition-cyclization of oxime ethers and hydrazones connected with alkenes for synthesis of cyclic β-amino acids". . p. 4459 - 4479. Retrieved 2007/10/03.
• 2、 Konosu,Oida. "Synthesis of racemic and optically active cispentacin (FR109615) using intramolecular nitrone-olefin cycloaddition". . p. 1012 - 1018. Retrieved 2007/10/02.