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

Base Information

• Chemical Name: 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
• CAS No.: 362673-21-0
• Molecular Formula: C₂₀H₂₂N₂O₆S
• Molecular Weight: 418.47

Synonyms: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

Chemical Property of 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

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Technology Process of 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

There total 6 articles about 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 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: 95.0%

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 (142967-22-4) → 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)

Guidance literature:

With iodoxy benzoic acid; In dimethyl sulfoxide; at 20 ℃; for 0.25h;

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

Reference yield:

cephaloram (859-07-4) → 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)

Guidance literature:

Multi-step reaction with 4 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

With 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) → 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)

Guidance literature:

Multi-step reaction with 5 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

With 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-(hydroxymethyl)-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

Downstream raw materials:

(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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