(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

Base Information

• Chemical Name: (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
• CAS No.: 362673-24-3
• Molecular Formula: C₂₀H₂₂N₂O₇S
• Molecular Weight: 434.47

Synonyms:(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

Chemical Property of (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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Technology Process of (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

There total 7 articles about (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 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: 80.0%

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 (362673-21-0) → (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 (362673-24-3)

Guidance literature:

With sodium chlorite; potassium dihydrogenphosphate; In tetrahydrofuran; at 0 - 20 ℃;

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

Reference yield:

cephaloram (859-07-4) → (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 (362673-24-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / MCPBA / CH₂Cl₂ / 1.5 h / 0 °C

2: immobilized cephalosporin acetyl hydrolase / H₂O / pH 7.5

3: 0.96 g / DCC / tetrahydrofuran

4: 95 percent / iodoxy benzoic acid / dimethylsulfoxide / 0.25 h / 20 °C

5: 80 percent / KH₂PO₄; NaClO₂ / tetrahydrofuran; various solvent(s) / 0 - 20 °C

With sodium chlorite; potassium dihydrogenphosphate; immobilized cephalosporin acetyl hydrolase; iodoxy benzoic acid; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide;

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)-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 (362673-24-3)

Guidance literature:

Multi-step reaction with 6 steps

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

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

3: immobilized cephalosporin acetyl hydrolase / H₂O / pH 7.5

4: 0.96 g / DCC / tetrahydrofuran

5: 95 percent / iodoxy benzoic acid / dimethylsulfoxide / 0.25 h / 20 °C

6: 80 percent / KH₂PO₄; NaClO₂ / tetrahydrofuran; various solvent(s) / 0 - 20 °C

With sodium chlorite; potassium dihydrogenphosphate; immobilized cephalosporin acetyl hydrolase; iodoxy benzoic acid; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; acetone; 1: Schotten-Baumann method;

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

upstream raw materials:

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

cephaloram

7-Aminocephalosporanic acid

phenylacetyl chloride

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