Unii-H9R95ET7JS

Base Information

• Chemical Name: Unii-H9R95ET7JS
• CAS No.: 111188-71-7
• Molecular Formula: C22H26 N2 O4 S
• Molecular Weight: 414.52
• UNII: H9R95ET7JS
• Nikkaji Number: J408.861A
• Mol file: 111188-71-7.mol

Synonyms:UNII-H9R95ET7JS;111188-71-7;H9R95ET7JS;(2R,3S)-5-(2-(Dimethylamino)ethyl)-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate;[(2R,3S)-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1,5-benzothiazepin-3-yl] acetate;1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-5-(2-(dimethylamino)ethyl)-2,3-dihydro-2-(4-methoxyphenyl)-, (2R,3S)-;1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-5-(2-(dimethylamino)ethyl)-2,3-dihydro-2-(4-methoxyphenyl)-, (2R-trans)-;Diltiazem hydrochloride impurity A [EP];DILTIAZEM HYDROCHLORIDE IMPURITY A [EP IMPURITY];(2R,3S)-5-(2-(Dimethylamino)ethyl)-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-yl acetate

Chemical Property of Unii-H9R95ET7JS

Chemical Property:

• PSA: 84.38000
• LogP: 3.43350
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 414.16132849
• Heavy Atom Count: 29
• Complexity: 565

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C(SC2=CC=CC=C2N(C1=O)CCN(C)C)C3=CC=C(C=C3)OC
• Isomeric SMILES: CC(=O)O[C@@H]1[C@H](SC2=CC=CC=C2N(C1=O)CCN(C)C)C3=CC=C(C=C3)OC

Technology Process of Unii-H9R95ET7JS

There total 15 articles about Unii-H9R95ET7JS 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:

ethyl (Z)-2-(2-methoxyethoxy)methoxy-3-(4-methoxyphenyl)-2-propenoate (154076-93-4) → (+/-)-Diltiazem (34933-06-7,42399-41-7,56209-45-1,75472-92-3,84675-89-8,84675-91-2,85100-18-1,111188-70-6,111188-71-7)

Guidance literature:

Multi-step reaction with 5 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 → (+/-)-Diltiazem (34933-06-7,42399-41-7,56209-45-1,75472-92-3,84675-89-8,84675-91-2,85100-18-1,111188-70-6,111188-71-7)

Guidance literature:

Multi-step reaction with 6 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

Reference yield:

ethyl 3-fluoro-2-<(2-methoxyethoxy)methoxy>-3-(4-methoxylphenyl)-2-propionate → (+/-)-Diltiazem (34933-06-7,42399-41-7,56209-45-1,75472-92-3,84675-89-8,84675-91-2,85100-18-1,111188-70-6,111188-71-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 59 percent / DBU / 9 h / 150 °C

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; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; xylene;

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

upstream raw materials:

acetic anhydride

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

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

ethyl (Z)-2-(2-methoxyethoxy)methoxy-3-(4-methoxyphenyl)-2-propenoate

Downstream raw materials:

{2-[3c-acetoxy-2r-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazepin-5-yl]-ethyl}-ethyl-dimethyl-ammonium; bromide

{2-[3c-acetoxy-2r-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazepin-5-yl]-ethyl}-trimethyl-ammonium; iodide

{2-[3c-acetoxy-2r-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazepin-5-yl]-ethyl}-dimethyl-propyl-ammonium; bromide

L-cis-diltiazem