(7R,7aR)-3-[(acetyloxy)methyl]-1,6-dioxo-7-[(2-phenylacetyl)amino]-1,6,7,7a-tetrahydro-2H-1λ⁴-azeto[2,1-b][1,3]thiazine-4-carboxylic acid

Base Information

• Chemical Name: (7R,7aR)-3-[(acetyloxy)methyl]-1,6-dioxo-7-[(2-phenylacetyl)amino]-1,6,7,7a-tetrahydro-2H-1λ⁴-azeto[2,1-b][1,3]thiazine-4-carboxylic acid
• CAS No.: 102779-37-3
• Molecular Formula: C₁₈H₁₈N₂O₇S
• Molecular Weight: 406.416

Synonyms:(7R,7aR)-3-[(acetyloxy)methyl]-1,6-dioxo-7-[(2-phenylacetyl)amino]-1,6,7,7a-tetrahydro-2H-1λ⁴-azeto[2,1-b][1,3]thiazine-4-carboxylic acid

Chemical Property of (7R,7aR)-3-[(acetyloxy)methyl]-1,6-dioxo-7-[(2-phenylacetyl)amino]-1,6,7,7a-tetrahydro-2H-1λ⁴-azeto[2,1-b][1,3]thiazine-4-carboxylic acid

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Technology Process of (7R,7aR)-3-[(acetyloxy)methyl]-1,6-dioxo-7-[(2-phenylacetyl)amino]-1,6,7,7a-tetrahydro-2H-1λ⁴-azeto[2,1-b][1,3]thiazine-4-carboxylic acid

There total 3 articles about (7R,7aR)-3-[(acetyloxy)methyl]-1,6-dioxo-7-[(2-phenylacetyl)amino]-1,6,7,7a-tetrahydro-2H-1λ⁴-azeto[2,1-b][1,3]thiazine-4-carboxylic 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: 98.0%

cephaloram (859-07-4) → (7R,7aR)-3-[(acetyloxy)methyl]-1,6-dioxo-7-[(2-phenylacetyl)amino]-1,6,7,7a-tetrahydro-2H-1λ4-azeto[2,1-b][1,3]thiazine-4-carboxylic acid (102779-37-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1002/1099-0690(200107)2001:13<2529::AID-EJOC2529>3.0.CO;2-9

Reference yield:

7-Aminocephalosporanic acid (957-68-6) → (7R,7aR)-3-[(acetyloxy)methyl]-1,6-dioxo-7-[(2-phenylacetyl)amino]-1,6,7,7a-tetrahydro-2H-1λ4-azeto[2,1-b][1,3]thiazine-4-carboxylic acid (102779-37-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / aq. NaHCO₃ / acetone / 17 h / 20 °C / pH 8.0

2: 98 percent / MCPBA / CH₂Cl₂ / 1.5 h / 0 °C

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetone; 1: Schotten-Baumann method;

DOI:10.1002/1099-0690(200107)2001:13<2529::AID-EJOC2529>3.0.CO;2-9

Reference yield:

phenylacetyl chloride (103-80-0) → (7R,7aR)-3-[(acetyloxy)methyl]-1,6-dioxo-7-[(2-phenylacetyl)amino]-1,6,7,7a-tetrahydro-2H-1λ4-azeto[2,1-b][1,3]thiazine-4-carboxylic acid (102779-37-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / aq. NaHCO₃ / acetone / 17 h / 20 °C / pH 8.0

2: 98 percent / MCPBA / CH₂Cl₂ / 1.5 h / 0 °C

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetone; 1: Schotten-Baumann method;

DOI:10.1002/1099-0690(200107)2001:13<2529::AID-EJOC2529>3.0.CO;2-9

upstream raw materials:

cephaloram

7-Aminocephalosporanic acid

phenylacetyl chloride

Downstream raw materials:

(5S,6R,7R)-3-Hydroxymethyl-5,8-dioxo-7-phenylacetylamino-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

tert-butyl (7R,7aR)-3-formyl-1,6-dioxo-7-[(2-phenylacetyl)amino]-1,6,7,7a-tetrahydro-2H-1λ⁴-azeto[2,1-b][1,3]thiazine-4-carboxylate

tert-butyl (7R,7aR)-3-(hydroxymethyl)-1,6-dioxo-7-[(2-phenylacetyl)amino]-1,6,7,7a-tetrahydro-2H-1λ⁴-azeto[2,1-b][1,3]thiazine-4-carboxylate

(7R,7aR)-4-(tert-butoxycarbonyl)-1,6-dioxo-7-[(2-phenylacetyl)amino]-1,6,7,7a-tetrahydro-2H-1λ⁴-azeto[2,1-b][1,3]thiazine-3-carboxylic acid

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