2-((2R,5S,6R)-6-(3-chlorophenyl)-5-(4-chlorophenyl)-4-(cyclopropylmethyl)-3-oxomorpholin-2-yl)acetic acid

Base Information

• Chemical Name: 2-((2R,5S,6R)-6-(3-chlorophenyl)-5-(4-chlorophenyl)-4-(cyclopropylmethyl)-3-oxomorpholin-2-yl)acetic acid
• CAS No.: 1432669-60-7
• Molecular Formula: C₂₂H₂₁Cl₂NO₄
• Molecular Weight: 434.319

Synonyms:2-((2R,5S,6R)-6-(3-chlorophenyl)-5-(4-chlorophenyl)-4-(cyclopropylmethyl)-3-oxomorpholin-2-yl)acetic acid

Chemical Property of 2-((2R,5S,6R)-6-(3-chlorophenyl)-5-(4-chlorophenyl)-4-(cyclopropylmethyl)-3-oxomorpholin-2-yl)acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 2-((2R,5S,6R)-6-(3-chlorophenyl)-5-(4-chlorophenyl)-4-(cyclopropylmethyl)-3-oxomorpholin-2-yl)acetic acid

There total 18 articles about 2-((2R,5S,6R)-6-(3-chlorophenyl)-5-(4-chlorophenyl)-4-(cyclopropylmethyl)-3-oxomorpholin-2-yl)acetic 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:

2-(6-(3-chlorophenyl)-5-(4-chlorophenyl)-4-(cyclopropylmethyl)-3-oxomorpholin-2-yl)acetic acid → 2-((2R,5S,6R)-6-(3-chlorophenyl)-5-(4-chlorophenyl)-4-(cyclopropylmethyl)-3-oxomorpholin-2-yl)acetic acid (1432669-60-7) + 2-((2S,5R,6S)-6-(3-chlorophenyl)-5-(4-chlorophenyl)-4-(cyclopropylmethyl)-3-oxomorpholin-2-yl)acetic acid (1432669-57-2)

Guidance literature:

With Chiralcel OD-H; In hexane; isopropyl alcohol;

Reference yield:

2-(4-Chlorophenyl)glycine (6212-33-5,7292-70-8) → 2-((2R,5S,6R)-6-(3-chlorophenyl)-5-(4-chlorophenyl)-4-(cyclopropylmethyl)-3-oxomorpholin-2-yl)acetic acid (1432669-60-7) + 2-((2S,5R,6S)-6-(3-chlorophenyl)-5-(4-chlorophenyl)-4-(cyclopropylmethyl)-3-oxomorpholin-2-yl)acetic acid (1432669-57-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: sodium hydroxide / 1,4-dioxane; water / 0.08 h / 0 °C / Inert atmosphere

1.2: 24 h / 20 °C / Inert atmosphere

2.1: 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

3.1: tetrahydrofuran / 0 - 25 °C / Inert atmosphere

4.1: sodium tetrahydroborate / tetrahydrofuran / 3 h / 0 - 25 °C / Inert atmosphere

5.1: trifluoroacetic acid / dichloromethane / 3.33 h / 0 - 25 °C / Inert atmosphere

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

6.2: 1 h / 20 °C / Inert atmosphere

6.3: 3 h / 20 °C / Inert atmosphere

7.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.37 h / 0 °C / Inert atmosphere

7.2: 4 h / 25 °C / Inert atmosphere; Enzymatic reaction

8.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.48 h / -78 °C / Inert atmosphere

8.2: 4 h / -78 °C / Inert atmosphere

9.1: 4-methylmorpholine N-oxide; potassium tetraoxo-osmate(VII) / water; tert-butyl alcohol; acetone / 25 °C / Inert atmosphere

10.1: sodium periodate / tetrahydrofuran / 4 h / 25 °C / pH 7 / Inert atmosphere

11.1: 2-methyl-but-2-ene; sodium chlorite; sodium dihydrogenphosphate / water; tert-butyl alcohol / 4 h / 0 - 25 °C / Inert atmosphere; Darkness

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

With sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; potassium tetraoxo-osmate(VII); sodium hexamethyldisilazane; sodium hydride; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetone; mineral oil; tert-butyl alcohol;

DOI:10.1021/jm400293z

Reference yield:

(±)-2-(tert-butoxycarbonyl)-2-(4-chlorophenyl)acetic Acid (53994-85-7) → 2-((2R,5S,6R)-6-(3-chlorophenyl)-5-(4-chlorophenyl)-4-(cyclopropylmethyl)-3-oxomorpholin-2-yl)acetic acid (1432669-60-7) + 2-((2S,5R,6S)-6-(3-chlorophenyl)-5-(4-chlorophenyl)-4-(cyclopropylmethyl)-3-oxomorpholin-2-yl)acetic acid (1432669-57-2)

Guidance literature:

Multi-step reaction with 11 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 / 0 - 25 °C / Inert atmosphere

3.1: sodium tetrahydroborate / tetrahydrofuran / 3 h / 0 - 25 °C / Inert atmosphere

4.1: trifluoroacetic acid / dichloromethane / 3.33 h / 0 - 25 °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 / 0.37 h / 0 °C / Inert atmosphere

6.2: 4 h / 25 °C / Inert atmosphere; Enzymatic reaction

7.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.48 h / -78 °C / Inert atmosphere

7.2: 4 h / -78 °C / Inert atmosphere

8.1: 4-methylmorpholine N-oxide; potassium tetraoxo-osmate(VII) / water; tert-butyl alcohol; acetone / 25 °C / Inert atmosphere

9.1: sodium periodate / tetrahydrofuran / 4 h / 25 °C / pH 7 / Inert atmosphere

10.1: 2-methyl-but-2-ene; sodium chlorite; sodium dihydrogenphosphate / water; tert-butyl alcohol / 4 h / 0 - 25 °C / Inert atmosphere; Darkness

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

With sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; potassium tetraoxo-osmate(VII); sodium hexamethyldisilazane; sodium hydride; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; mineral oil; tert-butyl alcohol;

DOI:10.1021/jm400293z

upstream raw materials:

2-(4-Chlorophenyl)glycine

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

(±)-tert-butyl 1-(4-chlorophenyl)-2-(methoxy(methyl)amino)-2-oxoethylcarbamate

(±)-tert-butyl 2-(3-chlorophenyl)-1-(4-chlorophenyl)-2-oxoethylcarbamate

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