Acromelic acid A

Base Information

• Chemical Name: Acromelic acid A
• CAS No.: 86630-09-3
• Molecular Formula: C₁₃H₁₄N₂O₇
• Molecular Weight: 310.263
• UNII: MDU5184Y3C
• DSSTox Substance ID: DTXSID70897146
• Nikkaji Number: J413.583K
• Metabolomics Workbench ID: 104533
• ChEMBL ID: CHEMBL4756304
• Mol file: 86630-09-3.mol

Synonyms:acromelic acid A

Chemical Property of Acromelic acid A

Chemical Property:

• Vapor Pressure: 5.44E-24mmHg at 25°C
• Boiling Point: 740.5°C at 760 mmHg
• Flash Point: 401.6°C
• PSA: 157.05000
• Density: 1.577g/cm³
• LogP: 0.04510
• XLogP3: -3.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 310.08010079
• Heavy Atom Count: 22
• Complexity: 608

Purity/Quality:

99% ^*data from raw suppliers

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=CC=C(NC2=O)C(=O)O
• Isomeric SMILES: C1[C@@H]([C@@H]([C@H](N1)C(=O)O)CC(=O)O)C2=CC=C(NC2=O)C(=O)O

Technology Process of Acromelic acid A

There total 74 articles about Acromelic acid A 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%

(2S,3S,4S)-1-((benzyloxy)carbonyl)-3-(2-methoxy-2-oxoethyl)-4-(2-methoxy-6-(methoxycarbonyl)pyridin-3-yl)pyrrolidine-2-carboxylic acid (1585241-73-1) → Acromelic acid A (86630-09-3)

Guidance literature:

With water; hydrogen bromide; In acetic acid; at 100 ℃; for 12h;

DOI:10.1021/ol500529w

Reference yield:

C8H6LiN → Acromelic acid A (86630-09-3)

Guidance literature:

Multi-step reaction with 16 steps

1: tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h / 1.) -70 deg C, 2.) r.t.

2: 85 percent / H₂, quinoline / Lindlar catalyst / benzene / 24 h / Ambient temperature

3: Et₃N / CH₂Cl₂ / 2 h / 0 °C

4: CH₂Cl₂ / 2 h / 0 °C

5: 73 percent / 1,2-dichloro-benzene / 1.5 h / 200 °C

6: H₂, HCl / 10percent Pd-C / methanol / 72 h / Ambient temperature

7: 3 N NaOH / dioxane / 1 h / Ambient temperature

8: 1.) aqueous NaIO₄, 2.) aq. KMnO₄ / 1.) 0 deg C, 15 min, 2.) 0 deg C, 2 h

9: c.c H₂SO₄ / 24 h / Heating

10: Et₃N / CH₂Cl₂ / 0.25 h / Ambient temperature

11: 94 percent / NaH, DBu / benzene / 5 h / Ambient temperature

12: m-CPBA / CH₂Cl₂ / 24 h / Ambient temperature

14: m-CPBA / CH₂Cl₂

15: trifluoroacetic anhydride / dimethylformamide / 45 h / Ambient temperature

With quinoline; hydrogenchloride; sodium hydroxide; potassium permanganate; sodium periodate; hydrogen; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; palladium on activated charcoal; Lindlar's catalyst; sulfuric acid; In tetrahydrofuran; 1,4-dioxane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; 1,2-dichloro-benzene; benzene;

DOI:10.1021/ja00252a037

Reference yield:

(R)-1-Benzyloxy-5-(6-methyl-pyridin-3-yl)-pent-4-yn-2-ol (109552-75-2) → Acromelic acid A (86630-09-3)

Guidance literature:

Multi-step reaction with 15 steps

1: 85 percent / H₂, quinoline / Lindlar catalyst / benzene / 24 h / Ambient temperature

2: Et₃N / CH₂Cl₂ / 2 h / 0 °C

3: CH₂Cl₂ / 2 h / 0 °C

4: 73 percent / 1,2-dichloro-benzene / 1.5 h / 200 °C

5: H₂, HCl / 10percent Pd-C / methanol / 72 h / Ambient temperature

6: 3 N NaOH / dioxane / 1 h / Ambient temperature

7: 1.) aqueous NaIO₄, 2.) aq. KMnO₄ / 1.) 0 deg C, 15 min, 2.) 0 deg C, 2 h

8: c.c H₂SO₄ / 24 h / Heating

9: Et₃N / CH₂Cl₂ / 0.25 h / Ambient temperature

10: 94 percent / NaH, DBu / benzene / 5 h / Ambient temperature

11: m-CPBA / CH₂Cl₂ / 24 h / Ambient temperature

13: m-CPBA / CH₂Cl₂

14: trifluoroacetic anhydride / dimethylformamide / 45 h / Ambient temperature

With quinoline; hydrogenchloride; sodium hydroxide; potassium permanganate; sodium periodate; hydrogen; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; palladium on activated charcoal; Lindlar's catalyst; sulfuric acid; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; 1,2-dichloro-benzene; benzene;

DOI:10.1021/ja00252a037

upstream raw materials:

methyl (3S,4S,5S)-5-<1-(tert-butyloxycarbonyl)-4-<(methoxycarbonyl)methyl>-5-(methoxycarbonyl)-3-pyrrolidinyl>-1,6-dihydro-6-oxo-2-pyridinecarboxylate

N-t-Boc-acromelic acid A

(2S,3S,4S)-3-Methoxycarbonylmethyl-4-(6-methoxycarbonyl-2-oxo-1,2-dihydro-pyridin-3-yl)-pyrrolidine-1,2-dicarboxylic acid 2-methyl ester 1-phenyl ester

[(2S,3S)-1-Benzoyl-4-(2,3-bis-benzyloxy-4-methoxy-phenyl)-2-hydroxymethyl-2,3-dihydro-1H-pyrrol-3-yl]-acetic acid tert-butyl ester

Refernces

• 1、 Ouchi, Hitoshi,Asahina, Aya,Asakawa, Tomohiro,Inai, Makoto,Hamashima, Yoshitaka,Kan, Toshiyuki. "Practical total syntheses of acromelic acids A and B". . p. 1980 - 1983. Retrieved 2014/05/06.
• 2、 Baldwin, Jack E.,Fryer, Andrew M.,Pritchard, Gareth J.,Spyvee, Mark R.,Whitehead, Roger C.,Wood, Mark E.. "Concise syntheses of acromelic acid A and allo-acromelic acid A". . p. 707 - 710. Retrieved 2007/10/03.