(1r,3r)-1-Aminocyclopentane-1,3-dicarboxylic acid

Base Information

• Chemical Name: (1r,3r)-1-Aminocyclopentane-1,3-dicarboxylic acid
• CAS No.: 111900-33-5
• Molecular Formula: C7H11 N O4
• Molecular Weight: 173.169
• European Community (EC) Number: 634-583-3,637-152-8
• NSC Number: 27386
• Nikkaji Number: J369.847E
• Wikipedia: ACPD
• ChEMBL ID: CHEMBL107845
• Mol file: 111900-33-5.mol

Synonyms:(trans)-1-aminocyclopentyl-1,3-dicarboxylate;1-amino-1,3-dicarboxycyclopentane;1-amino-1,3-dicarboxycyclopentane, (cis)-(+-)-isomer;1-amino-1,3-dicarboxycyclopentane, (trans)-(+-)-isomer;1-amino-1,3-dicarboxycyclopentane, (trans)-isomer;1-amino-1,3-dicarboxycyclopentane, cis-(1R,3R)-isomer;1-amino-1,3-dicarboxycyclopentane, cis-(1S,3S)-isomer;1-amino-1,3-dicarboxycyclopentane, trans-(1R,3S)-isomer;1-amino-cyclopentyl-trans-1S,3R-dicarboxylate;1-aminocyclopentane-1,3-dicarboxylic acid;1-aminocyclopentyl-1,3-dicarboxylic acid;1R,3S-ACPD;1S,3R-ACPD;ACPD-1S,3R;cis-1-amino-1,3-cyclopentanecarboxylic acid;cis-ACPD;t-ACPD;trans-1-aminocyclopentane-1,3-dicarboxylate;trans-ACPD

Chemical Property of (1r,3r)-1-Aminocyclopentane-1,3-dicarboxylic acid

Chemical Property:

• Melting Point: 277 °C (decomp)
• Boiling Point: 352.7±42.0 °C(Predicted)
• PKA: 2.11±0.40(Predicted)
• PSA: 100.62000
• Density: 1.452±0.06 g/cm3(Predicted)
• LogP: 0.35350
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 173.06880783
• Heavy Atom Count: 12
• Complexity: 227

Purity/Quality:

99% ^*data from raw suppliers

(1R,3R)-1-AMINOCYCLOPENTANE-1,3-DICARBOXYLIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(CC1C(=O)O)(C(=O)O)N
• Isomeric SMILES: C1C[C@@](C[C@@H]1C(=O)O)(C(=O)O)N

Technology Process of (1r,3r)-1-Aminocyclopentane-1,3-dicarboxylic acid

There total 23 articles about (1r,3r)-1-Aminocyclopentane-1,3-dicarboxylic 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: 66.0%

(1S,3S)-1-tert-Butoxycarbonylamino-3-cyano-cyclopentanecarboxylic acid ethyl ester → trans-(+/-)-1-amino-1,3-cyclopentanedicarboxylic acid (39026-63-6,39026-64-7,56827-69-1,67684-64-4,89253-38-3,100910-67-6,111900-31-3,111900-32-4,111900-33-5,477331-06-9)

Guidance literature:

With hydrogenchloride; ammonium hydroxide; Dowex 50WX₈-100; 1.) reflux, 4 h;

DOI:10.1016/S0040-4039(98)00490-0

Reference yield:

(5R,7S)-2,4-Dioxo-1,3-diaza-spiro[4.4]nonane-7-carboxylic acid (112896-82-9,112965-97-6,112965-98-7,112965-99-8,122743-40-2,122743-41-3) → trans-1-aminocyclopentane-1,3-dicarboxylic acid (39026-63-6,39026-64-7,56827-69-1,67684-64-4,89253-38-3,100910-67-6,111900-31-3,111900-32-4,111900-33-5,477331-06-9)

Guidance literature:

With barium(II) oxide; at 140 ℃;

DOI:10.1016/S0040-4039(00)82278-9

Reference yield:

(1S,3S)-3-Acetoxy-1-tert-butoxycarbonylamino-cyclopentanecarboxylic acid ethyl ester → trans-1-aminocyclopentane-1,3-dicarboxylic acid (39026-63-6,39026-64-7,56827-69-1,67684-64-4,89253-38-3,100910-67-6,111900-31-3,111900-32-4,111900-33-5,477331-06-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 66 percent / K₂CO₃ / ethanol

2: Et₃N / CH₂Cl₂ / 17 h / 0 deg C up to RT

3: dimethylformamide / 17 h / 80 °C

4: 1.) 6M HCl; 2.) Dowex 50WX₈-100, 2M aq. NH₃ / 1.) reflux, 4 h

With hydrogenchloride; ammonium hydroxide; Dowex 50WX₈-100; potassium carbonate; triethylamine; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(98)00490-0

upstream raw materials:

(1R,3S)-ACPD

trans-(+/-)-1-amino-1,3-cyclopentanedicarboxylic acid

(1R)-3-oxocyclopentane-1-carboxylic acid

(-)-(S)-3-oxocyclopentanecarboxylic acid

Downstream raw materials:

(1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic acid

(1R,3S)-ACPD

(1R,3R)-ACPD

(1S,3S)-ACPD