2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-N-methylpentanamido)-3-phenylpropanamido)ethylcarbamic acid benzyl ester

Base Information

• Chemical Name: 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-N-methylpentanamido)-3-phenylpropanamido)ethylcarbamic acid benzyl ester
• CAS No.: 1563182-83-1
• Molecular Formula: C₄₄H₄₈Cl₂FN₅O₆
• Molecular Weight: 832.799

Synonyms:2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-N-methylpentanamido)-3-phenylpropanamido)ethylcarbamic acid benzyl ester

Chemical Property of 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-N-methylpentanamido)-3-phenylpropanamido)ethylcarbamic acid benzyl ester

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Technology Process of 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-N-methylpentanamido)-3-phenylpropanamido)ethylcarbamic acid benzyl ester

There total 17 articles about 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-N-methylpentanamido)-3-phenylpropanamido)ethylcarbamic acid benzyl 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: 51.0%

6-fluoro-1-methylspiro[benzo[d][1,3]oxazine-4,4'-piperidin]-2(1H)-one (1036926-64-3) + 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methyl-5-oxopentanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester (1563182-81-9) → 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-N-methylpentanamido)-3-phenylpropanamido)ethylcarbamic acid benzyl ester (1563182-83-1)

Guidance literature:

6-fluoro-1-methylspiro[benzo[d][1,3]oxazine-4,4'-piperidin]-2(1H)-one; 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-N-methyl-5-oxopentanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester; In 1,2-dichloro-ethane; at 20 ℃; for 18h; Molecular sieve; Inert atmosphere;

With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/ml400528y

Reference yield:

N-Cbz-L-Phe (1161-13-3) → 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-N-methylpentanamido)-3-phenylpropanamido)ethylcarbamic acid benzyl ester (1563182-83-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: (1S)-10-camphorsulfonic acid / toluene / 0.5 h / Reflux; Inert atmosphere

1.2: 3 h / 20 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / methanol / 8 h / 20 °C

3.1: triethylamine / dichloromethane / 8 h / 0 - 20 °C / Inert atmosphere

4.1: triethylamine; benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane / 20 °C / Cooling with ice; Inert atmosphere

5.1: hydrogenchloride / 1,4-dioxane / 10 h / 20 °C / Inert atmosphere

6.1: 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere

6.2: 16 h / 20 °C / Inert atmosphere

7.1: Wilkinson's catalyst; benzo[1,3,2]dioxaborole / tetrahydrofuran / 6.5 h / 0 - 20 °C / Inert atmosphere

7.2: 12 h / 0 - 20 °C

8.1: Dess-Martin periodane / dichloromethane / 12 h / 20 °C / Inert atmosphere

9.1: 1,2-dichloro-ethane / 18 h / 20 °C / Molecular sieve; Inert atmosphere

9.2: 18 h / 20 °C / Inert atmosphere

With hydrogenchloride; Wilkinson's catalyst; palladium 10% on activated carbon; (1S)-10-camphorsulfonic acid; hydrogen; benzotriazol-1-ol; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; benzo[1,3,2]dioxaborole; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1021/ml400528y

Reference yield:

(S)-N-benzyloxycarbonyl-N-methyl-phenyl alanine (2899-07-2) → 2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-N-methylpentanamido)-3-phenylpropanamido)ethylcarbamic acid benzyl ester (1563182-83-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: palladium 10% on activated carbon; hydrogen / methanol / 8 h / 20 °C

2.1: triethylamine / dichloromethane / 8 h / 0 - 20 °C / Inert atmosphere

3.1: triethylamine; benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane / 20 °C / Cooling with ice; Inert atmosphere

4.1: hydrogenchloride / 1,4-dioxane / 10 h / 20 °C / Inert atmosphere

5.1: 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere

5.2: 16 h / 20 °C / Inert atmosphere

6.1: Wilkinson's catalyst; benzo[1,3,2]dioxaborole / tetrahydrofuran / 6.5 h / 0 - 20 °C / Inert atmosphere

6.2: 12 h / 0 - 20 °C

7.1: Dess-Martin periodane / dichloromethane / 12 h / 20 °C / Inert atmosphere

8.1: 1,2-dichloro-ethane / 18 h / 20 °C / Molecular sieve; Inert atmosphere

8.2: 18 h / 20 °C / Inert atmosphere

With hydrogenchloride; Wilkinson's catalyst; palladium 10% on activated carbon; hydrogen; benzotriazol-1-ol; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; benzo[1,3,2]dioxaborole; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/ml400528y

upstream raw materials:

N-Cbz-L-Phe

(S)-N-benzyloxycarbonyl-N-methyl-phenyl alanine

N-(tert-butoxycarbonyl)-4-fluoroaniline

N-tert-butyloxycarbonylpiperidin-4-one

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