(1R,2S)-2-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid

Base Information

• Chemical Name: (1R,2S)-2-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid
• CAS No.: 130981-12-3
• Molecular Formula: C11H19NO4
• Molecular Weight: 229.276
• Hs Code.: 2922498590
• European Community (EC) Number: 812-188-9,853-832-9
• DSSTox Substance ID: DTXSID40361460
• Nikkaji Number: J1.975.441C
• Wikidata: Q76119935
• Mol file: 130981-12-3.mol

Synonyms:130981-12-3;136315-70-3;(1R,2S)-2-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid;(1R,2S)-2-(Boc-amino)cyclopentanecarboxylic Acid;cis-2-tert-Butoxycarbonylamino-cyclopentanecarboxylic acid;cis-2-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid;(1R,2S)-2-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid;Cis-2-(tert-butoxycarbonylamino)-1-cyclopentanecarboxylic acid;(1R,2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylic acid;cis-2-Bocamino-cyclopentanecarboxylic acid;MFCD00800539;(1R,2S)-2-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylic acid;(1R,2S)-2-{[(tert-butoxy)carbonyl]amino}cyclopentane-1-carboxylic acid;(1R,2S)-Boc-2-amino-1-cyclopentanecarboxylic acid;(1R,2S)-2-((tert-butoxycarbonyl)amino)cyclopentane-1-carboxylic acid;(1R,2S)-2-[(tert-butoxycarbonyl)amino]cyclopentane-1-carboxylic acid;cis-2-(Boc-amino)cyclopentanecarboxylic Acid;MFCD09750530;cis-2-Boc-amino-cyclopentanecarboxylic acid;boc-cis-acpc, AldrichCPR;SCHEMBL82642;DTXSID40361460;AMY19367;AKOS015996117;AS-32528;BB 0260166;CS-0089894;EN300-195776;F20540;(1r,2s)-2-BOC-aminocyclopentanecarboxylic acid;(1R,2S)-2-Boc-amino-cyclopentanecarboxylic acid;A888645;RAC CIS-2-BOCAMINO-CYCLOPENTANECARBOXYLIC ACID;N-Boc-(+/-)cis-2-amino-cyclopentane-1-carboxylic acid;(+/-)-cis-2-(Boc-amino)cyclopentanecarboxylic acid, >=97.0%;rac-cis-2-(tert-butoxycarbonylamino)-cyclopentanecarboxylic acid;(1R,2S)-2-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylicacid;2beta-[(tert-Butyloxycarbonyl)amino]cyclopentane-1beta-carboxylic acid;CIS-2-(TERT-BUTOXYCARBONYLAMINO)-1-CYCLOPENTANECARBOXYLIC ACID, 98;CIS-2-(TERT-BUTOXYCARBONYLAMINO)-1-CYCLOPENTANECARBOXYLICACID,98;Cyclopentanecarboxylic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, (1R,2S)-

Chemical Property of (1R,2S)-2-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid

Chemical Property:

• Vapor Pressure: 6.55E-07mmHg at 25°C
• Melting Point: 124-127 °C
• Boiling Point: 382.5°C at 760 mmHg
• PKA: 4.53±0.40(Predicted)
• Flash Point: 185.1°C
• PSA: 75.63000
• Density: 1.15g/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:

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

(1R,2S)-2-(tert-Butoxycarbonylamino)cyclopentanecarboxylic acid 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

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

Technology Process of (1R,2S)-2-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid

There total 21 articles about (1R,2S)-2-((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: 100.0%

C19H27NO4 → (-)-N-(tert-butyloxycarbonyl)-cis-2-aminocyclopentanecarboxylic acid (130981-12-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20 ℃; for 5h; under 760.051 Torr;

DOI:10.1002/anie.201800169

Reference yield: 91.0%

(1S,2R)-1-(tert-butoxycarbonylamino)-2-<(1R*,2R*)-1,2-dihydroxypropyl>cyclopentane (145213-16-7) → (-)-N-(tert-butyloxycarbonyl)-cis-2-aminocyclopentanecarboxylic acid (130981-12-3)

Guidance literature:

With potassium permanganate; sodium periodate; dipotassium hydrogenphosphate; potassium dihydrogenphosphate; In water; acetone; for 3h; Ambient temperature;

DOI:10.1248/cpb.41.1012

Reference yield: 82.0%

tert-butyl ((1S,2R)-2-(hydroxymethyl)cyclopentyl)carbamate (623582-54-7) → (-)-N-(tert-butyloxycarbonyl)-cis-2-aminocyclopentanecarboxylic acid (130981-12-3)

Guidance literature:

With sodium periodate; ruthenium trichloride; In water; acetonitrile; at 20 ℃; for 2h;

DOI:10.1021/jo034940o

upstream raw materials:

(1S,2R)-1-(tert-butoxycarbonylamino)-2-<(1R^*,2R^*)-1,2-dihydroxypropyl>cyclopentane

(±)-cis-2-((tert-butoxycarbonyl)amino)cyclopentanecarboxylic acid

tert-butyl ((1S,2R)-2-(hydroxymethyl)cyclopentyl)carbamate

hex-5-en-1-al

Downstream raw materials:

C₆H₁₂N₂O*(x)ClH

trifluoroacetic acid

Refernces

• 1、 Wang, Shengyang,Sun, Jiansong,Zhang, Qingju,Cao, Xin,Zhao, Yachen,Tang, Gongli,Yu, Biao. "Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers". . p. 2884 - 2888. Retrieved 2018/02/16.
• 2、 Konosu,Oida. "Synthesis of racemic and optically active cispentacin (FR109615) using intramolecular nitrone-olefin cycloaddition". . p. 1012 - 1018. Retrieved 2007/10/02.