(E)-2-Acetylamino-3-{4-[4-methoxy-3-(6-methoxy-pyridin-3-ylmethyl)-phenoxy]-3,5-dimethyl-phenyl}-acrylic acid

Base Information

• Chemical Name: (E)-2-Acetylamino-3-{4-[4-methoxy-3-(6-methoxy-pyridin-3-ylmethyl)-phenoxy]-3,5-dimethyl-phenyl}-acrylic acid
• CAS No.: 105189-73-9
• Molecular Formula: C₂₇H₂₈N₂O₆
• Molecular Weight: 476.529

Synonyms:(E)-2-Acetylamino-3-{4-[4-methoxy-3-(6-methoxy-pyridin-3-ylmethyl)-phenoxy]-3,5-dimethyl-phenyl}-acrylic acid

Chemical Property of (E)-2-Acetylamino-3-{4-[4-methoxy-3-(6-methoxy-pyridin-3-ylmethyl)-phenoxy]-3,5-dimethyl-phenyl}-acrylic acid

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Technology Process of (E)-2-Acetylamino-3-{4-[4-methoxy-3-(6-methoxy-pyridin-3-ylmethyl)-phenoxy]-3,5-dimethyl-phenyl}-acrylic acid

There total 9 articles about (E)-2-Acetylamino-3-{4-[4-methoxy-3-(6-methoxy-pyridin-3-ylmethyl)-phenoxy]-3,5-dimethyl-phenyl}-acrylic 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: 80.0%

4-[1-{4-[4-Methoxy-3-(6-methoxy-pyridin-3-ylmethyl)-phenoxy]-3,5-dimethyl-phenyl}-meth-(E)-ylidene]-2-methyl-4H-oxazol-5-one (105211-20-9) → (E)-2-Acetylamino-3-{4-[4-methoxy-3-(6-methoxy-pyridin-3-ylmethyl)-phenoxy]-3,5-dimethyl-phenyl}-acrylic acid (105189-73-9)

Guidance literature:

With sodium hydroxide; In ethanol; at 65 ℃; for 0.5h;

DOI:10.1021/jm00122a009

Reference yield:

2-methoxy-5-bromopyridine (13472-85-0,1199266-76-6) → (E)-2-Acetylamino-3-{4-[4-methoxy-3-(6-methoxy-pyridin-3-ylmethyl)-phenoxy]-3,5-dimethyl-phenyl}-acrylic acid (105189-73-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) n-BuLi / 1) THF, hexane, -85 deg C, 5 min, 2) THF, below -70 deg C to room temperature

2: pyridine / 50 °C

3: H₂ / 10percent Pd/C / methanol

4: 1) iodine tris(trifluoroacetate), 2) NaClO₄ / 1) CF₃COOH, (CF₃CO)2O, room temperature, overnight, 2) CH₂Cl₂, H₂O, NaAc

5: Cu bronze, dicyclohexyl-18-crown-6, KOBu-t / CH₂Cl₂ / 4 h

6: 64 percent / NaOAc / acetic anhydride / 24 h / 100 °C

7: 80 percent / 2 N NaOH / ethanol / 0.5 h / 65 °C

With pyridine; perhydrodibenzo-18-crown-6; sodium hydroxide; n-butyllithium; copper bronze; iodine tris(trifluoroacetate); potassium tert-butylate; sodium perchlorate; hydrogen; sodium acetate; palladium on activated charcoal; In methanol; ethanol; dichloromethane; acetic anhydride;

DOI:10.1021/jm00122a009

Reference yield:

ortho-anisaldehyde (135-02-4) → (E)-2-Acetylamino-3-{4-[4-methoxy-3-(6-methoxy-pyridin-3-ylmethyl)-phenoxy]-3,5-dimethyl-phenyl}-acrylic acid (105189-73-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) n-BuLi / 1) THF, hexane, -85 deg C, 5 min, 2) THF, below -70 deg C to room temperature

2: pyridine / 50 °C

3: H₂ / 10percent Pd/C / methanol

4: 1) iodine tris(trifluoroacetate), 2) NaClO₄ / 1) CF₃COOH, (CF₃CO)2O, room temperature, overnight, 2) CH₂Cl₂, H₂O, NaAc

5: Cu bronze, dicyclohexyl-18-crown-6, KOBu-t / CH₂Cl₂ / 4 h

6: 64 percent / NaOAc / acetic anhydride / 24 h / 100 °C

7: 80 percent / 2 N NaOH / ethanol / 0.5 h / 65 °C

With pyridine; perhydrodibenzo-18-crown-6; sodium hydroxide; n-butyllithium; copper bronze; iodine tris(trifluoroacetate); potassium tert-butylate; sodium perchlorate; hydrogen; sodium acetate; palladium on activated charcoal; In methanol; ethanol; dichloromethane; acetic anhydride;

DOI:10.1021/jm00122a009

upstream raw materials:

4-[1-{4-[4-Methoxy-3-(6-methoxy-pyridin-3-ylmethyl)-phenoxy]-3,5-dimethyl-phenyl}-meth-(E)-ylidene]-2-methyl-4H-oxazol-5-one

2-methoxy-5-bromopyridine

ortho-anisaldehyde

2-<(2-methoxypyrid-5-yl)methyl>anisole

Downstream raw materials:

3,5-dimethyl-O-methyl-3'-<(2-oxo-1,2-dihydropyrid-5-yl)methyl>-DL-thyronine

N-acetyl-3,5-dimethyl-O-methyl-3'-<(2-methoxypyrid-5-yl)methyl>-DL-thyronine

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