Cyclopentanecarboxylic acid, 2-amino-4-methylene-, (1R,2S)- (9CI)

Base Information

• Chemical Name: Cyclopentanecarboxylic acid, 2-amino-4-methylene-, (1R,2S)- (9CI)
• CAS No.: 198022-65-0
• Molecular Formula: C7H11 N O2
• Molecular Weight: 141.17
• Hs Code.: 2916399090
• Mol file: 198022-65-0.mol

Synonyms:Cyclopentanecarboxylicacid, 2-amino-4-methylene-, (1R-cis)-; BAY 10-8888; Icofungipen; PLD 118

Chemical Property of Cyclopentanecarboxylic acid, 2-amino-4-methylene-, (1R,2S)- (9CI)

Chemical Property:

• Vapor Pressure: 0.00123mmHg at 25°C
• Boiling Point: 277.4°C at 760 mmHg
• Flash Point: 121.6°C
• PSA: 63.32000
• Density: 1.16g/cm³
• LogP: 1.06480

Purity/Quality:

97% ^*data from raw suppliers

(1R,2S)-2-AMINO-4-METHYLENECYCLOPENTANECARBOXYLIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cyclopentanecarboxylic acid, 2-amino-4-methylene-, (1R,2S)- (9CI)

There total 14 articles about Cyclopentanecarboxylic acid, 2-amino-4-methylene-, (1R,2S)- (9CI) 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: 85.0%

(2E)-3-phenyl-2-propenyl (1R,2S)-4-methylene-2-{[(2E)-3-phenyl-2-propenyloxycarbonyl]amino}cyclopentanecarboxylate (198022-62-7) → (-)-(1R,2S)-2-amino-4-methylenecyclopentanecarboxylic acid (198022-65-0,156292-16-9,156292-48-7,755750-29-9,526194-96-7,786615-32-5)

Guidance literature:

With morpholine; palladium diacetate; triphenylphosphine; In ethanol;

DOI:10.1016/S0960-894X(02)00958-7

Reference yield:

→ isoleucine (319-78-8,443-79-8,1509-34-8,1509-35-9,3107-04-8,7004-09-3,73-32-5,959215-79-3,18875-42-8) + (-)-(1R,2S)-2-amino-4-methylenecyclopentanecarboxylic acid (198022-65-0,156292-16-9,156292-48-7,755750-29-9,526194-96-7,786615-32-5)

Guidance literature:

Reference yield:

1,2,3,4-butanetetracarboxylic acid (4534-68-3) → (-)-(1R,2S)-2-amino-4-methylenecyclopentanecarboxylic acid (198022-65-0,156292-16-9,156292-48-7,755750-29-9,526194-96-7,786615-32-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: H₂SO₄ / toluene / 9 h / Heating

2.1: NaOMe / methanol / 1 h / 20 °C

3.1: aq. HCl / methanol / 20 - 57 °C

4.1: aq. HCl / 5 h / 100 °C

5.1: 1.72 kg / H₂SO₄ / 4 h / Heating

6.1: t-BuOK / tetrahydrofuran / 2 h / 20 °C

6.2: tetrahydrofuran / 2 h / -15 - 10 °C

7.1: 145 g / aq. KOH / tetrahydrofuran / 20 °C

8.1: 75 percent / (EtCO)2O / 8 h / 135 °C

9.1: 84 percent / (R)-(6-methoxyquinolin-4-yl)-(5-vinyl-1-azabicyclo[2.2.2]...; dihydroquinine / toluene / -15 °C

10.1: (PhO)2PON₃; Et₃N / toluene / 0.5 h / 90 °C

11.1: 62.0 g / toluene / Heating

12.1: 85 percent / Ph₃P; morpholine; Pd(OAc)2 / ethanol / 2 h / Heating

With morpholine; hydrogenchloride; palladium diacetate; potassium hydroxide; (R)-(6-methoxyquinolin-4-yl)-(5-vinyl-1-azabicyclo[2.2.2]..; sulfuric acid; diphenyl phosphoryl azide; potassium tert-butylate; sodium methylate; propionic acid anhydride; triethylamine; triphenylphosphine; dihydroquinine; In tetrahydrofuran; methanol; ethanol; toluene; 2.1: Dieckmann cyclization / 6.2: Wittig reaction / 10.1: Curtius rearrangement;

DOI:10.1055/s-2003-36265

upstream raw materials:

(2E)-3-phenyl-2-propenyl (1R,2S)-4-methylene-2-{[(2E)-3-phenyl-2-propenyloxycarbonyl]amino}cyclopentanecarboxylate

1,2,3,4-butanetetracarboxylic acid

1,2,3,4-butanetetracarboxylic acid tetraethyl ester

4-Methylene-cyclopentane-1,2-dicarboxylic acid diethyl ester

Downstream raw materials:

(+)-(1R,2S)-2-amino-4-methyl-cyclopent-3-enecarboxylic acid

(-)-(1R,5S)-5-amino-3-methyl-cyclopent-2-enecarboxylic acid

Refernces

• 1、 Mittendorf, Joachim,Benet-Buchholz, Jordi,Fey, Peter,Mohrs, Klaus-Helmut. "Efficient asymmetric synthesis of β-amino acid BAY 10-8888/PLD-118, a novel antifungal for the treatment of yeast infections". . p. 136 - 140. Retrieved 2007/10/03.
• 2、 -. "Efficient and highly enantioselective process for the preparation of enantiomerically pure cyclopentane-β-amino acids". . . Retrieved 2008/06/13.