((2S,4R)-2-Oxo-2-phenyl-3,4-dihydro-2λ⁶-thieno[3,2-c][1,2]thiazin-4-yl)-acetic acid methyl ester

Base Information

• Chemical Name: ((2S,4R)-2-Oxo-2-phenyl-3,4-dihydro-2λ⁶-thieno[3,2-c][1,2]thiazin-4-yl)-acetic acid methyl ester
• CAS No.: 540484-04-6
• Molecular Formula: C₁₅H₁₅NO₃S₂
• Molecular Weight: 321.421

Synonyms:((2S,4R)-2-Oxo-2-phenyl-3,4-dihydro-2λ⁶-thieno[3,2-c][1,2]thiazin-4-yl)-acetic acid methyl ester

Chemical Property of ((2S,4R)-2-Oxo-2-phenyl-3,4-dihydro-2λ⁶-thieno[3,2-c][1,2]thiazin-4-yl)-acetic acid methyl ester

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Technology Process of ((2S,4R)-2-Oxo-2-phenyl-3,4-dihydro-2λ⁶-thieno[3,2-c][1,2]thiazin-4-yl)-acetic acid methyl ester

There total 3 articles about ((2S,4R)-2-Oxo-2-phenyl-3,4-dihydro-2λ⁶-thieno[3,2-c][1,2]thiazin-4-yl)-acetic 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: 91.3%

C15H15NO3S2 → ((2S,4R)-2-Oxo-2-phenyl-3,4-dihydro-2λ6-thieno[3,2-c][1,2]thiazin-4-yl)-acetic acid methyl ester (540484-04-6)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1021/ja034744z

Reference yield:

3-bromo-2-thiophenecarboxaldehyde (930-96-1) → ((2S,4R)-2-Oxo-2-phenyl-3,4-dihydro-2λ6-thieno[3,2-c][1,2]thiazin-4-yl)-acetic acid methyl ester (540484-04-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran / 0.17 h / 0 °C

1.2: 88 percent / tetrahydrofuran / 4 h / 0 - 20 °C

2.1: 77.6 percent / Pd(OAc)2; BINAP; Cs₂CO₃ / toluene / 44 h / 110 °C

3.1: 91.3 percent / LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

With palladium diacetate; n-butyllithium; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; lithium hexamethyldisilazane; In tetrahydrofuran; toluene; 1.2: Wittig olefination;

DOI:10.1021/ja034744z

Reference yield:

methyl trans-β-(3-bromo-2-thienyl)acrylate (91150-50-4) → ((2S,4R)-2-Oxo-2-phenyl-3,4-dihydro-2λ6-thieno[3,2-c][1,2]thiazin-4-yl)-acetic acid methyl ester (540484-04-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 77.6 percent / Pd(OAc)2; BINAP; Cs₂CO₃ / toluene / 44 h / 110 °C

2: 91.3 percent / LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; lithium hexamethyldisilazane; In tetrahydrofuran; toluene;

DOI:10.1021/ja034744z

upstream raw materials:

3-bromo-2-thiophenecarboxaldehyde

methyl trans-β-(3-bromo-2-thienyl)acrylate

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