(1R,3S)-3-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid

Base Information

• Chemical Name: (1R,3S)-3-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid
• CAS No.: 161660-94-2
• Molecular Formula: C11H19NO4
• Molecular Weight: 229.276
• Hs Code.: 29223900
• European Community (EC) Number: 851-929-0
• DSSTox Substance ID: DTXSID70936569
• Nikkaji Number: J3.248.288K
• Mol file: 161660-94-2.mol

Synonyms:161660-94-2;(1R,3S)-3-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid;410090-37-8;(-)-(1R,3S)-N-BOC-3-AMINOCYCLOPENTANECARBOXYLIC ACID;cis-3-(Boc-amino)cyclopentanecarboxylic Acid;(1R,3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylic acid;(1R,3S)-3-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid;(1R,3S)-3-{[(tert-butoxy)carbonyl]amino}cyclopentane-1-carboxylic acid;(1R,3S)-Boc-3-aminocyclopentane-1 carboxylic acid;CIS-3-(BOC-AMINO)CYCLOPENTANE-1-CARBOXYLIC ACID;(1R,3S)-3-(BOC-amino)cyclopentanecarboxylic acid;cis-3-(N-tert-Butoxycarbonylamino)cyclopentanecarboxylic acid;MFCD01320858;(1R,3S)-3-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylic acid;MFCD09992879;(1R,3S)-N-Boc-1-Aminocyclopentane-3-carboxylic acid;Boc-cis-NH(3)cPen-OH;(1R,3S)-(-)-3-(Boc-amino)cyclopentanecarboxylic Acid;cis-3-(tert-Butoxycarbonylamino)cyclopentanecarboxylic acid;(1R,3S)-3-Boc-amino-cyclopentanecarboxylic acid;SCHEMBL540505;(1R,3S)-3-(Boc-amino)cyclopentane-1-carboxylic acid;(-)-(1R,3S)-N-Boc-3-aminocyclopentane carboxylic acid;DTXSID70936569;(1R,3S)-3-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylicacid;(1R,3S)-3-((tert-butoxycarbonyl)amino)cyclopentane-1-carboxylic acid;AKOS016344288;AC-7961;CS-W004812;DS-14793;BB 0260212;EN300-1589930;(1R,3S)-N-Boc-3-Aminocyclopentanecarboxylic acid;A1-52905;J-500347;(1R,3S)-n-boc-3-aminocyclopentane-1-carboxylic acid;(-)-(1s,3r)-n-boc-aminocyclopentane-3-carboxylic acid;(-)-(1s, 3r)-n-boc-aminocyclopentane-3-carboxylic acid;(1R,3S)-3-t-Butoxycarbonylaminocyclopentanecarboxylic acid;(1R,3S)-3-(t-butoxycarbonylamino)cyclopentanecarboxylic acid;(1R,3S)-3-tert-butoxycarbonylamino-cyclopentanecarboxylic acid;cis-3-((tert-butoxycarbonyl)amino)cyclopentanecarboxylic acid;(1beta)-3beta-(tert-Butoxycarbonylamino)cyclopentanecarboxylic acid;(1S,3R)-rel-3-{[(tert-butoxy)carbonyl]amino}cyclopentane-1-carboxylic acid;cis(1R,3S)-3-((tert-butoxycarbonyl)amino) cyclopentanecarboxylic acid;(1R,3S)-3-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)cyclopentanecarboxylic acid;Cyclopentanecarboxylic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-, (1R,3S)-

Chemical Property of (1R,3S)-3-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 6.55E-07mmHg at 25°C
• Melting Point: 96.1 °C
• Refractive Index: 1.4490 (estimate)
• Boiling Point: 382.5 °C at 760 mmHg
• PKA: 4.62±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: 1.4
• 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:

97% ^*data from raw suppliers

(1R,3S)-3-[(tert-Butoxycarbonyl)amino]cyclopentanecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1CCC(C1)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H]1CC[C@H](C1)C(=O)O
• Uses: (1R,3S)-3-[(tert-Butoxycarbonyl)amino]cyclopentanecarboxylic Acid is used as a reagent in the sunthesis of Jak1 kinase inhibitors stemming from tricyclic pyrrolopyrazines.

Technology Process of (1R,3S)-3-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid

There total 13 articles about (1R,3S)-3-((tert-Butoxycarbonyl)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: 99.0%

(1S-cis)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-cyclopentene-1-carboxylic acid (151907-79-8,108999-93-5) → (1R,3S)-3-((tert-butoxycarbonyl)amino)cyclopentane-1-carboxylic acid (161660-94-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; for 12h;

DOI:10.1002/ejoc.201201565

Reference yield:

2-azabicyclo[2.2.1.]hept-5-en-3-one (49805-30-3) → (1R,3S)-3-((tert-butoxycarbonyl)amino)cyclopentane-1-carboxylic acid (161660-94-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / H₂ / Pd/C / ethyl acetate

2: 93 percent / aq. HCl / 48 h / 20 °C

3: DIEA / H₂O; dioxane / 3 h / 20 °C

With hydrogenchloride; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; water; ethyl acetate;

DOI:10.1002/anie.200501555

Reference yield:

(1R,4S)-tert-butyl 3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate (204913-00-8) → (1R,3S)-3-((tert-butoxycarbonyl)amino)cyclopentane-1-carboxylic acid (161660-94-2)

Guidance literature:

Product distribution / selectivity;

upstream raw materials:

cis-3-aminocyclopentanecarboxylic acid hydrochloride

di-tert-butyl dicarbonate

2-Azabicyclo[2.2.1]heptan-3-one

2-azabicyclo[2.2.1.]hept-5-en-3-one

Downstream raw materials:

(1S,4R)-1-tert-butoxycarbonylamino-4-hydroxymethylcyclopentane

tert-butyl (1S,3R)-3-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarbonyl)cyclopentylcarbamate

1-((3R)-1-{[(1R,3S)-aminocyclopentyl]carbonyl}-3-piperidinyl)-5-(methyloxy)-1-[2-(phenyloxy)phenyl]-1-pentanol trifluoroacetate