(R)-3-benzyloxy-2-(3-carbamoyl-2,4-difluoro-phenoxy)propionic acid methyl ester

Base Information

• Chemical Name: (R)-3-benzyloxy-2-(3-carbamoyl-2,4-difluoro-phenoxy)propionic acid methyl ester
• CAS No.: 1403884-02-5
• Molecular Formula: C₁₈H₁₇F₂NO₅
• Molecular Weight: 365.333

Synonyms:(R)-3-benzyloxy-2-(3-carbamoyl-2,4-difluoro-phenoxy)propionic acid methyl ester

Chemical Property of (R)-3-benzyloxy-2-(3-carbamoyl-2,4-difluoro-phenoxy)propionic acid methyl ester

Chemical Property:

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Technology Process of (R)-3-benzyloxy-2-(3-carbamoyl-2,4-difluoro-phenoxy)propionic acid methyl ester

There total 4 articles about (R)-3-benzyloxy-2-(3-carbamoyl-2,4-difluoro-phenoxy)propionic acid methyl ester 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: 53.0%

2,6-difluoro-3-hydroxy-benzamide (951122-37-5) + (S)-methyl 3-(benzyloxy)-2-hydroxypropanoate (127744-28-9) → (R)-3-benzyloxy-2-(3-carbamoyl-2,4-difluoro-phenoxy)propionic acid methyl ester (1403884-02-5)

Guidance literature:

With triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20 ℃; for 48.66h;

Reference yield:

BOC-O-benzyl-L-serine (23680-31-1) → (R)-3-benzyloxy-2-(3-carbamoyl-2,4-difluoro-phenoxy)propionic acid methyl ester (1403884-02-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trifluoroacetic acid / 0.75 h / 20 °C

1.2: 20 h / 5 - 20 °C / pH 4

2.1: sulfuric acid / 16 h / Reflux

3.1: triethylamine; triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 48.66 h / 0 - 20 °C

With sulfuric acid; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran;

Reference yield:

2,6-difluoro-3-methoxybenzamide → (R)-3-benzyloxy-2-(3-carbamoyl-2,4-difluoro-phenoxy)propionic acid methyl ester (1403884-02-5)

Guidance literature:

Multi-step reaction with 2 steps

1: boron tribromide / dichloromethane / 48 h / 20 °C / Inert atmosphere

2: triphenylphosphine; diethylazodicarboxylate; triethylamine / tetrahydrofuran / 48 h / 0 - 20 °C

With boron tribromide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 2: |Mitsunobu Displacement;

DOI:10.1016/j.bmcl.2013.11.002

upstream raw materials:

BOC-O-benzyl-L-serine

2,6-difluoro-3-hydroxy-benzamide

(S)-methyl 3-(benzyloxy)-2-hydroxypropanoate

Downstream raw materials:

(R)-3-(2-(benzyloxy)-1-(6-chlorothiazolo[5,4-b]pyridin-2-yl)ethoxy)-2,6-difluorobenzonitrile

(R)-3-(1-(6-chlorothiazolo[5,4-b]pyridin-2-yl)-2-hydroxyethoxy)-2,6-difluorobenzamide

(R)-4-(2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethoxy)-4-oxobutanoic acid

(R)-4-(2-(5-bromo-4-(4-(trifluoromethyl)phenyl)oxazol-2-yl)-2-(3-carbamoyl-2,4-difluorophenoxy)ethoxy)-4-oxobutanoic acid L-arginine salt

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