((2R,4R)-8-Methoxy-6-methyl-2-oxo-2-phenyl-3,4-dihydro-2λ⁶-benzo[c][1,2]thiazin-4-yl)-acetic acid methyl ester

Base Information

• Chemical Name: ((2R,4R)-8-Methoxy-6-methyl-2-oxo-2-phenyl-3,4-dihydro-2λ⁶-benzo[c][1,2]thiazin-4-yl)-acetic acid methyl ester
• CAS No.: 540484-10-4
• Molecular Formula: C₁₉H₂₁NO₄S
• Molecular Weight: 359.446

Synonyms:((2R,4R)-8-Methoxy-6-methyl-2-oxo-2-phenyl-3,4-dihydro-2λ⁶-benzo[c][1,2]thiazin-4-yl)-acetic acid methyl ester

Chemical Property of ((2R,4R)-8-Methoxy-6-methyl-2-oxo-2-phenyl-3,4-dihydro-2λ⁶-benzo[c][1,2]thiazin-4-yl)-acetic acid methyl ester

Chemical Property:

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Technology Process of ((2R,4R)-8-Methoxy-6-methyl-2-oxo-2-phenyl-3,4-dihydro-2λ⁶-benzo[c][1,2]thiazin-4-yl)-acetic acid methyl ester

There total 2 articles about ((2R,4R)-8-Methoxy-6-methyl-2-oxo-2-phenyl-3,4-dihydro-2λ⁶-benzo[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: 53.0%

(R)-S-methyl-S-phenylsulfoximine (60933-65-5) + (E)-3-(2-Bromo-3-methoxy-5-methyl-phenyl)-acrylic acid methyl ester → C19H21NO4S + ((2R,4R)-8-Methoxy-6-methyl-2-oxo-2-phenyl-3,4-dihydro-2λ6-benzo[c][1,2]thiazin-4-yl)-acetic acid methyl ester (540484-10-4)

Guidance literature:

With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; for 44h; Heating;

DOI:10.1021/ja034744z

Reference yield:

2-bromo-3-methoxy-5-methylbenzaldehyde (202195-05-9) → ((2R,4R)-8-Methoxy-6-methyl-2-oxo-2-phenyl-3,4-dihydro-2λ6-benzo[c][1,2]thiazin-4-yl)-acetic acid methyl ester (540484-10-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / CH₂Cl₂ / Heating

2: 36 percent / Pd(OAc)2; BINAP; Cs₂CO₃ / toluene / 44 h / Heating

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

DOI:10.1021/ja034744z

Reference yield: 92.0%

lithium tert-butoxide (1907-33-1) + ((2R,4R)-8-Methoxy-6-methyl-2-oxo-2-phenyl-3,4-dihydro-2λ6-benzo[c][1,2]thiazin-4-yl)-acetic acid methyl ester (540484-10-4) → C22H27NO4S (945526-89-6)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 11h;

DOI:10.1021/ol0710358

upstream raw materials:

(R)-S-methyl-S-phenylsulfoximine

2-bromo-3-methoxy-5-methylbenzaldehyde

Downstream raw materials:

C₂₂H₂₇NO₄S

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