(4S,7S,9aR)-7-Benzyl-6,9-dioxo-octahydro-pyrazino[2,1-c][1,4]thiazine-4-carboxylic acid methyl ester

Base Information

• Chemical Name: (4S,7S,9aR)-7-Benzyl-6,9-dioxo-octahydro-pyrazino[2,1-c][1,4]thiazine-4-carboxylic acid methyl ester
• CAS No.: 131700-03-3
• Molecular Formula: C₁₆H₁₈N₂O₄S
• Molecular Weight: 334.396

Synonyms:(4S,7S,9aR)-7-Benzyl-6,9-dioxo-octahydro-pyrazino[2,1-c][1,4]thiazine-4-carboxylic acid methyl ester

Chemical Property of (4S,7S,9aR)-7-Benzyl-6,9-dioxo-octahydro-pyrazino[2,1-c][1,4]thiazine-4-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (4S,7S,9aR)-7-Benzyl-6,9-dioxo-octahydro-pyrazino[2,1-c][1,4]thiazine-4-carboxylic acid methyl ester

There total 5 articles about (4S,7S,9aR)-7-Benzyl-6,9-dioxo-octahydro-pyrazino[2,1-c][1,4]thiazine-4-carboxylic 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: 35.0%

Z-Phe-(3R-cis)-Tht(OMe)-OMe (131700-01-1) → (4R,7S,9aS)-7-Benzyl-6,9-dioxo-octahydro-pyrazino[2,1-c][1,4]thiazine-4-carboxylic acid methyl ester (131726-55-1) + (4S,7S,9aR)-7-Benzyl-6,9-dioxo-octahydro-pyrazino[2,1-c][1,4]thiazine-4-carboxylic acid methyl ester (131700-03-3)

Guidance literature:

With hydrogen; palladium/alumina; In dichloromethane; acetic acid; for 24h;

DOI:10.1002/jhet.5570270627

Reference yield:

Dimethyl (3R-cis)-tetrahydro-1,4-thiazine-3,5-dicarboxylate (88422-73-5) → (4S,7S,9aR)-7-Benzyl-6,9-dioxo-octahydro-pyrazino[2,1-c][1,4]thiazine-4-carboxylic acid methyl ester (131700-03-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / pyridine / diethyl ether / 3 h / Ambient temperature

2: 56 percent / hydrogen / 10 percent palladium on alumina / CH₂Cl₂; acetic acid / 24 h

With pyridine; hydrogen; palladium/alumina; In diethyl ether; dichloromethane; acetic acid;

DOI:10.1002/jhet.5570270627

Reference yield:

N-Cbz-L-Phe (1161-13-3) → (4S,7S,9aR)-7-Benzyl-6,9-dioxo-octahydro-pyrazino[2,1-c][1,4]thiazine-4-carboxylic acid methyl ester (131700-03-3)

Guidance literature:

Multi-step reaction with 3 steps

1: phosphorus pentachloride / diethyl ether / 0.33 h / 0 °C

2: 40 percent / pyridine / diethyl ether / 3 h / Ambient temperature

3: 56 percent / hydrogen / 10 percent palladium on alumina / CH₂Cl₂; acetic acid / 24 h

With pyridine; phosphorus pentachloride; hydrogen; palladium/alumina; In diethyl ether; dichloromethane; acetic acid;

DOI:10.1002/jhet.5570270627

upstream raw materials:

Z-Phe-(3R-cis)-Tht(OMe)-OMe

Dimethyl (3R-cis)-tetrahydro-1,4-thiazine-3,5-dicarboxylate

N-Cbz-L-Phe

5-Ethyl 3-methyl (3R-cis)-tetrahydro-1,4-thiazine-3,5-dicarboxylate

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