(2RS,3RS)-cis-2,3-dihydro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

Base Information

• Chemical Name: (2RS,3RS)-cis-2,3-dihydro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one
• CAS No.: 42399-53-1
• Molecular Formula: C₂₀H₂₄N₂O₃S
• Molecular Weight: 372.488
• Mol file: 42399-53-1.mol

Synonyms:(2RS,3RS)-cis-2,3-dihydro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

Chemical Property of (2RS,3RS)-cis-2,3-dihydro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2RS,3RS)-cis-2,3-dihydro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

There total 22 articles about (2RS,3RS)-cis-2,3-dihydro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one 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: 93.9%

3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one (27068-88-8,30825-34-4,42399-49-5,42399-51-9,89646-44-6,101143-20-8,107438-58-4,132830-16-1,132830-17-2) + (2-chloroethyl)dimethylamine hydrochloride (4584-46-7) → 5-(2-dimethylamino-ethyl)-3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one (23515-44-8,36913-08-3,42399-39-3,42399-40-6,42399-53-1,91926-65-7,91926-66-8,91926-67-9,97229-67-9)

Guidance literature:

With potassium carbonate; In ethyl acetate; for 8h; Heating;

DOI:10.1248/cpb.45.1922

Reference yield:

ethyl (Z)-2-(2-methoxyethoxy)methoxy-3-(4-methoxyphenyl)-2-propenoate (154076-93-4) → 5-(2-dimethylamino-ethyl)-3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one (23515-44-8,36913-08-3,42399-39-3,42399-40-6,42399-53-1,91926-65-7,91926-66-8,91926-67-9,97229-67-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent Spectr_. / BuLi / tetrahydrofuran / 5 h / 70 °C

2: 5percent aq. NaOH / Ambient temperature

3: 7 percent / 4 Angstroem molecular sieves / xylene / Heating

4: K₂CO₃

With sodium hydroxide; n-butyllithium; 4 A molecular sieve; potassium carbonate; In tetrahydrofuran; xylene;

DOI:10.1016/S0040-4020(01)88031-5

Reference yield:

3-Hydroxy-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionic acid ethyl ester → 5-(2-dimethylamino-ethyl)-3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one (23515-44-8,36913-08-3,42399-39-3,42399-40-6,42399-53-1,91926-65-7,91926-66-8,91926-67-9,97229-67-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 49 percent / Et₃N, 2-fluoro-1-methylpyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h / Ambient temperature

2: 85 percent Spectr_. / BuLi / tetrahydrofuran / 5 h / 70 °C

3: 5percent aq. NaOH / Ambient temperature

4: 7 percent / 4 Angstroem molecular sieves / xylene / Heating

5: K₂CO₃

With sodium hydroxide; n-butyllithium; 4 A molecular sieve; potassium carbonate; 1-methyl-2-fluoropyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; dichloromethane; xylene;

DOI:10.1016/S0040-4020(01)88031-5

upstream raw materials:

2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

2-(dimethylamino)ethyl chloride

3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one

(2-chloroethyl)dimethylamine hydrochloride

Downstream raw materials:

3-methyl-butyric acid 5-(2-dimethylamino-ethyl)-2c-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3r-yl ester

(+/-)-Diltiazem

3c-butyryloxy-5-(2-dimethylamino-ethyl)-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one

O-desacetyldiltiazem