(R)-2-((2S,5R,6S)-2-(4-fluorobenzyl)-5,6-bis(4-chlorophenyl)-3-oxomorpholino)pentanoic acid

Base Information

• Chemical Name: (R)-2-((2S,5R,6S)-2-(4-fluorobenzyl)-5,6-bis(4-chlorophenyl)-3-oxomorpholino)pentanoic acid
• CAS No.: 1432669-51-6
• Molecular Formula: C₂₈H₂₆Cl₂FNO₄
• Molecular Weight: 530.423

Synonyms:(R)-2-((2S,5R,6S)-2-(4-fluorobenzyl)-5,6-bis(4-chlorophenyl)-3-oxomorpholino)pentanoic acid

Chemical Property of (R)-2-((2S,5R,6S)-2-(4-fluorobenzyl)-5,6-bis(4-chlorophenyl)-3-oxomorpholino)pentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (R)-2-((2S,5R,6S)-2-(4-fluorobenzyl)-5,6-bis(4-chlorophenyl)-3-oxomorpholino)pentanoic acid

There total 15 articles about (R)-2-((2S,5R,6S)-2-(4-fluorobenzyl)-5,6-bis(4-chlorophenyl)-3-oxomorpholino)pentanoic 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: 100.0%

(R)-ethyl 2-((2S,5R,6S)-2-(4-fluorobenzyl)-5,6-bis(4-chlorophenyl)-3-oxomorpholino)pentanoate (1432669-80-1) → (R)-2-((2S,5R,6S)-2-(4-fluorobenzyl)-5,6-bis(4-chlorophenyl)-3-oxomorpholino)pentanoic acid (1432669-51-6)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 25 ℃; for 4h; Inert atmosphere;

DOI:10.1021/jm400293z

Reference yield:

(±)-tert-butyl 1-(4-chlorophenyl)-2-(methoxy(methyl)amino)-2-oxoethylcarbamate (1239611-22-3) → (R)-2-((2S,5R,6S)-2-(4-fluorobenzyl)-5,6-bis(4-chlorophenyl)-3-oxomorpholino)pentanoic acid (1432669-51-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

3.1: trifluoroacetic acid / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

4.1: triethylamine / tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere

4.2: 1 h / 20 °C / Inert atmosphere

4.3: 3 h / 20 °C / Inert atmosphere

5.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.33 h / 0 °C / Inert atmosphere

5.2: 16 h / 25 °C / Inert atmosphere

6.1: Chiralcel OD-H / Resolution of racemate; Inert atmosphere

7.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

8.1: lithium hydroxide / methanol; tetrahydrofuran; water / 4 h / 25 °C / Inert atmosphere

With sodium tetrahydroborate; sodium hydride; triethylamine; trifluoroacetic acid; lithium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jm400293z

Reference yield:

(±)-2-(tert-butoxycarbonyl)-2-(4-chlorophenyl)acetic Acid (53994-85-7) → (R)-2-((2S,5R,6S)-2-(4-fluorobenzyl)-5,6-bis(4-chlorophenyl)-3-oxomorpholino)pentanoic acid (1432669-51-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

3.1: sodium tetrahydroborate / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

4.1: trifluoroacetic acid / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

5.1: triethylamine / tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere

5.2: 1 h / 20 °C / Inert atmosphere

5.3: 3 h / 20 °C / Inert atmosphere

6.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.33 h / 0 °C / Inert atmosphere

6.2: 16 h / 25 °C / Inert atmosphere

7.1: Chiralcel OD-H / Resolution of racemate; Inert atmosphere

8.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

9.1: lithium hydroxide / methanol; tetrahydrofuran; water / 4 h / 25 °C / Inert atmosphere

With sodium tetrahydroborate; sodium hydride; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jm400293z

upstream raw materials:

(R)-ethyl 2-((2S,3R)-2,3-bis(4-chlorophenyl)-5-oxomorpholino)pentanoate

4-Fluorobenzyl bromide

2-(4-Chlorophenyl)glycine

(±)-2-(tert-butoxycarbonyl)-2-(4-chlorophenyl)acetic Acid

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