Acromelic acid E

Base Information

• Chemical Name: Acromelic acid E
• CAS No.: 145237-01-0
• Deprecated CAS: 180467-60-1
• Molecular Formula: C₁₃H₁₄N₂O₆
• Molecular Weight: 294.264
• DSSTox Substance ID: DTXSID60162951
• Wikidata: Q83031771
• Metabolomics Workbench ID: 143943
• Mol file: 145237-01-0.mol

Synonyms:Acromelic acid E;(-)-Acromelic acid E;145237-01-0;2-Pyridinecarboxylic acid, 3-((3S,4S,5S)-5-carboxy-4-(carboxymethyl)-3-pyrrolidinyl)-;2-Pyridinecarboxylic acid, 3-(5-carboxy-4-(carboxymethyl)-3-pyrrolidinyl)-, (3S-(3alpha,4alpha,5beta))-;DTXSID60162951

Chemical Property of Acromelic acid E

Chemical Property:

• Vapor Pressure: 1.54E-16mmHg at 25°C
• Refractive Index: 1.601
• Boiling Point: 626°C at 760 mmHg
• Flash Point: 332.4°C
• Density: 1.477g/cm³
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 294.08518617
• Heavy Atom Count: 21
• Complexity: 440

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(N1)C(=O)O)CC(=O)O)C2=C(N=CC=C2)C(=O)O
• Isomeric SMILES: C1[C@@H]([C@@H]([C@H](N1)C(=O)O)CC(=O)O)C2=C(N=CC=C2)C(=O)O

Technology Process of Acromelic acid E

There total 20 articles about Acromelic acid E 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:

(2S,3S,4S)-3-Carboxymethyl-4-(2-methoxycarbonyl-pyridin-3-yl)-pyrrolidine-1,2-dicarboxylic acid dimethyl ester → acromelic acid E (145237-01-0)

Guidance literature:

With potassium hydroxide; at 120 ℃; Yield given;

DOI:10.1016/S0040-4039(00)60580-4

Reference yield:

3-pyridinylethanol (6293-56-7) → acromelic acid E (145237-01-0)

Guidance literature:

Multi-step reaction with 18 steps

1: mCPBA

2: Me₂NCOCl / CH₂Cl₂

3: methanol

4: CH₂Cl₂

5: 70 percent / KH / CH₂Cl₂ / Ambient temperature

6: 1) BF₃ * MeOH, 2) NaBH₄ / 1) 120 deg C

7: imidazole

8: 1) O₃, 2) NaH / 1) methanol, -78 deg C, 2) CH₂Cl₂, -78 deg C

9: MsCl, Et₃N

10: CSA / ethanol

11: Dess-Martin periodinane (DMP)

12: 2) Dess-Martin periodinane (DMP) / 1) irradiation, toluene, -78 deg C

13: 98 percent / methanol

14: Dess-Martin periodinane (DMP)

15: NaClO₂, NaH₂PO₄ / various solvent(s)

17: 1) HCO₂H, 2) H₂O / 2) 140 deg C

18: 3 N KOH / 120 °C

With 1H-imidazole; potassium hydroxide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; formic acid; camphor-10-sulfonic acid; water; boron trifluoride methanol complex; potassium hydride; sodium hydride; Dess-Martin periodane; ozone; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; N,N-Dimethylcarbamoyl chloride; In methanol; ethanol; dichloromethane;

DOI:10.1016/S0040-4039(00)60580-4

Reference yield:

methyl pyridine-3-acetate (39998-25-9) → acromelic acid E (145237-01-0)

Guidance literature:

Multi-step reaction with 19 steps

1: LiAlH₄

2: mCPBA

3: Me₂NCOCl / CH₂Cl₂

4: methanol

5: CH₂Cl₂

6: 70 percent / KH / CH₂Cl₂ / Ambient temperature

7: 1) BF₃ * MeOH, 2) NaBH₄ / 1) 120 deg C

8: imidazole

9: 1) O₃, 2) NaH / 1) methanol, -78 deg C, 2) CH₂Cl₂, -78 deg C

10: MsCl, Et₃N

11: CSA / ethanol

12: Dess-Martin periodinane (DMP)

13: 2) Dess-Martin periodinane (DMP) / 1) irradiation, toluene, -78 deg C

14: 98 percent / methanol

15: Dess-Martin periodinane (DMP)

16: NaClO₂, NaH₂PO₄ / various solvent(s)

18: 1) HCO₂H, 2) H₂O / 2) 140 deg C

19: 3 N KOH / 120 °C

With 1H-imidazole; potassium hydroxide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; lithium aluminium tetrahydride; formic acid; camphor-10-sulfonic acid; water; boron trifluoride methanol complex; potassium hydride; sodium hydride; Dess-Martin periodane; ozone; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; N,N-Dimethylcarbamoyl chloride; In methanol; ethanol; dichloromethane;

DOI:10.1016/S0040-4039(00)60580-4

upstream raw materials:

3-pyridinylethanol

methyl pyridine-3-acetate

3-pyridineacetic acid hydrochloride

2-(1-Oxy-pyridin-3-yl)-ethanol

Refernces