2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methyl-4-oxobutanamido)-2-phenylacetamido)ethyl carbamic acid tert-butyl ester

Base Information

• Chemical Name: 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methyl-4-oxobutanamido)-2-phenylacetamido)ethyl carbamic acid tert-butyl ester
• CAS No.: 1563182-87-5
• Molecular Formula: C₂₆H₃₁Cl₂N₃O₅
• Molecular Weight: 536.455

Synonyms:2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methyl-4-oxobutanamido)-2-phenylacetamido)ethyl carbamic acid tert-butyl ester

Chemical Property of 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methyl-4-oxobutanamido)-2-phenylacetamido)ethyl carbamic acid tert-butyl ester

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Technology Process of 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methyl-4-oxobutanamido)-2-phenylacetamido)ethyl carbamic acid tert-butyl ester

There total 3 articles about 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methyl-4-oxobutanamido)-2-phenylacetamido)ethyl carbamic acid tert-butyl 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:

2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methylpent-4-enamido)-2-phenylacetamido)ethyl carbamic acid tert-butyl ester (1563182-86-4) → 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methyl-4-oxobutanamido)-2-phenylacetamido)ethyl carbamic acid tert-butyl ester (1563182-87-5)

Guidance literature:

2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methylpent-4-enamido)-2-phenylacetamido)ethyl carbamic acid tert-butyl ester; With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; at 20 ℃; for 3h; Darkness;

With sodium periodate; In tetrahydrofuran; water; at 20 ℃; for 12h;

DOI:10.1021/ml400528y

Reference yield:

3,4-dichlorophenyl acetic acid (5807-30-7) → 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methyl-4-oxobutanamido)-2-phenylacetamido)ethyl carbamic acid tert-butyl ester (1563182-87-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran; pentane / 2 h / -25 °C / Inert atmosphere

1.2: 1.27 h / -25 - 20 °C / Inert atmosphere

2.1: ethyl acetate / Resolution of racemate; Inert atmosphere

3.1: hydrogenchloride / ethyl acetate; water

4.1: N-ethyl-N,N-diisopropylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere

5.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water / 3 h / 20 °C / Darkness

5.2: 12 h / 20 °C

With hydrogenchloride; osmium(VIII) oxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; water; ethyl acetate; pentane;

DOI:10.1021/ml400528y

Reference yield:

C8H11N*C11H10Cl2O2 (1563182-41-1) → 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methyl-4-oxobutanamido)-2-phenylacetamido)ethyl carbamic acid tert-butyl ester (1563182-87-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogenchloride / ethyl acetate; water

2.1: N-ethyl-N,N-diisopropylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere

3.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water / 3 h / 20 °C / Darkness

3.2: 12 h / 20 °C

With hydrogenchloride; osmium(VIII) oxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; water; ethyl acetate;

DOI:10.1021/ml400528y

upstream raw materials:

3,4-dichlorophenyl acetic acid

C₈H₁₁N*C₁₁H₁₀Cl₂O₂

2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methylpent-4-enamido)-2-phenylacetamido)ethyl carbamic acid tert-butyl ester

Downstream raw materials:

2-((S)-2-((R)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-N-methyl butanamido)-2-phenylacetamido)ethyl carbamic acid tert-butyl ester

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