methyl (E)-4-(3-oxo-3-(((tetrahydro-2H-pyran-2-yl)oxy)amino)propan-1-en-1-yl)benzoate

Base Information

• Chemical Name: methyl (E)-4-(3-oxo-3-(((tetrahydro-2H-pyran-2-yl)oxy)amino)propan-1-en-1-yl)benzoate
• CAS No.: 1143460-71-2
• Molecular Formula: C₁₆H₁₉NO₅
• Molecular Weight: 305.331

Synonyms:methyl (E)-4-(3-oxo-3-(((tetrahydro-2H-pyran-2-yl)oxy)amino)propan-1-en-1-yl)benzoate

Chemical Property of methyl (E)-4-(3-oxo-3-(((tetrahydro-2H-pyran-2-yl)oxy)amino)propan-1-en-1-yl)benzoate

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Technology Process of methyl (E)-4-(3-oxo-3-(((tetrahydro-2H-pyran-2-yl)oxy)amino)propan-1-en-1-yl)benzoate

There total 3 articles about methyl (E)-4-(3-oxo-3-(((tetrahydro-2H-pyran-2-yl)oxy)amino)propan-1-en-1-yl)benzoate 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: 90.0%

O-2-tetrahydro-2H-pyranhydroxylamine (6723-30-4) + (E)-4-(methoxycarbonyl)cinnamic acid (117390-07-5) → methyl (E)-4-(3-oxo-3-(((tetrahydro-2H-pyran-2-yl)oxy)amino)propan-1-en-1-yl)benzoate (1143460-71-2)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In N,N-dimethyl-formamide; for 8h; Inert atmosphere; Cooling with ice;

DOI:10.1021/acs.jmedchem.9b02161

Reference yield:

tetrahydro-2H-2-pyranol (694-54-2) + (E)-4-(methoxycarbonyl)cinnamic acid (117390-07-5) → methyl (E)-4-(3-oxo-3-(((tetrahydro-2H-pyran-2-yl)oxy)amino)propan-1-en-1-yl)benzoate (1143460-71-2)

Guidance literature:

(E)-4-(methoxycarbonyl)cinnamic acid; With 4-methyl-morpholine; chloroformic acid ethyl ester; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

tetrahydro-2H-2-pyranol; With triethylamine; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1248/cpb.c14-00449

Reference yield:

methyl 4-formylbenzoate (1571-08-0) → methyl (E)-4-(3-oxo-3-(((tetrahydro-2H-pyran-2-yl)oxy)amino)propan-1-en-1-yl)benzoate (1143460-71-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: piperidine; pyridine / 3 h / 85 °C / Inert atmosphere

2.1: 4-methyl-morpholine; chloroformic acid ethyl ester / tetrahydrofuran / 1 h / 0 - 20 °C

2.2: 1 h / 0 °C

With piperidine; 4-methyl-morpholine; pyridine; chloroformic acid ethyl ester; In tetrahydrofuran;

DOI:10.1248/cpb.c14-00449

upstream raw materials:

O-2-tetrahydro-2H-pyranhydroxylamine

(E)-4-(methoxycarbonyl)cinnamic acid

methyl 4-formylbenzoate

tetrahydro-2H-2-pyranol

Downstream raw materials:

(E)-4-(3-oxo-3-(((tetrahydro-2H-pyran-2-yl)-oxy)amino)prop-1-en-1-yl)benzoic acid

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