(R)-4-(5-chlorobenzo[d]oxazol-2-yl)-7-Methyl-1,4-diazepan-1-iuM (2S,3S)-2,3-bis(benzoyloxy)-3-carboxypropanoate

Base Information

• Chemical Name: (R)-4-(5-chlorobenzo[d]oxazol-2-yl)-7-Methyl-1,4-diazepan-1-iuM (2S,3S)-2,3-bis(benzoyloxy)-3-carboxypropanoate
• CAS No.: 1276666-14-8
• Molecular Formula: C31H30ClN3O9
• Molecular Weight: 624.047
• Mol file: 1276666-14-8.mol

Synonyms:(R)-4-(5-chlorobenzo[d]oxazol-2-yl)-7-Methyl-1,4-diazepan-1-iuM (2S,3S)-2,3-bis(benzoyloxy)-3-carboxypropanoate;(5R)-4-(5-Chloro-1,3-benzoxazol-2-yl)-5-methyl-1,4-diazepan-1-ium (2S,3S)-2,3-bis(benzoyloxy)butanedioate

Chemical Property of (R)-4-(5-chlorobenzo[d]oxazol-2-yl)-7-Methyl-1,4-diazepan-1-iuM (2S,3S)-2,3-bis(benzoyloxy)-3-carboxypropanoate

Chemical Property:

• Melting Point: 164.2℃
• PSA: 168.50000
• LogP: 4.67000

Purity/Quality:

99.9% ^*data from raw suppliers

Butanedioicacid,2,3-bis(benzoyloxy)-,(2S,3S)-,compd.with5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole1:1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-4-(5-chlorobenzo[d]oxazol-2-yl)-7-Methyl-1,4-diazepan-1-iuM (2S,3S)-2,3-bis(benzoyloxy)-3-carboxypropanoate

There total 8 articles about (R)-4-(5-chlorobenzo[d]oxazol-2-yl)-7-Methyl-1,4-diazepan-1-iuM (2S,3S)-2,3-bis(benzoyloxy)-3-carboxypropanoate 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:

O,O'-dibenzoyl-D-tartaric acid (17026-42-5) + 5-chloro-2-(5-methyl-[1,4]diazepan-1-yl)-benzoxazole (1276666-13-7) → C13H16ClN3O*C18H14O8 (1276666-16-0) + C13H16ClN3O*C18H14O8 (1276666-14-8)

Guidance literature:

O,O'-dibenzoyl-D-tartaric acid; 5-chloro-2-(5-methyl-[1,4]diazepan-1-yl)-benzoxazole; In tetrahydrofuran; at 20 ℃; for 4.91667h; Resolution of racemate;

With Isopropyl acetate; In methanol; at 20 ℃; for 22.25h; optical yield given as %ee; Resolution of racemate;

DOI:10.1021/op1002853

Reference yield:

5-chloro-2-mercaptobenzoxazole (22876-19-3) → C13H16ClN3O*C18H14O8 (1276666-16-0) + C13H16ClN3O*C18H14O8 (1276666-14-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dichloromethane; N,N-dimethyl-formamide / 1.75 h / 20 - 25 °C

2.1: triethylamine / dichloromethane / 2.5 h / 0 - 20 °C

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane; water; acetonitrile / 10.08 h / 20 - 40 °C

4.1: tetrahydrofuran / 5 - 60 °C

5.1: sodium acetate; sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 15 - 20 °C

6.1: tetrahydrofuran / 4.92 h / 20 °C / Resolution of racemate

6.2: 22.25 h / 20 °C / Resolution of racemate

With sodium acetate; sodium tris(acetoxy)borohydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 3.1: Aza-Michael reaction;

DOI:10.1021/op1002853

Reference yield:

2-hydroxy-5-chloro-aniline (95-85-2) → C13H16ClN3O*C18H14O8 (1276666-16-0) + C13H16ClN3O*C18H14O8 (1276666-14-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: methanol; water / 2 h / 0 - 20 °C

2.1: dichloromethane; N,N-dimethyl-formamide / 1.75 h / 20 - 25 °C

3.1: triethylamine / dichloromethane / 2.5 h / 0 - 20 °C

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane; water; acetonitrile / 10.08 h / 20 - 40 °C

5.1: tetrahydrofuran / 5 - 60 °C

6.1: sodium acetate; sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 15 - 20 °C

7.1: tetrahydrofuran / 4.92 h / 20 °C / Resolution of racemate

7.2: 22.25 h / 20 °C / Resolution of racemate

With sodium acetate; sodium tris(acetoxy)borohydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 4.1: Aza-Michael reaction;

DOI:10.1021/op1002853

upstream raw materials:

(2-((5-chloro-1,3-benzoxazol-2-yl)amino)ethyl)carbamic acid tert-butyl ester

5-chloro-2-mercaptobenzoxazole

2,5-dichloro-1,3-benzoxazole

O,O'-dibenzoyl-D-tartaric acid

Downstream raw materials:

Suvorexant

Refernces

• 1、 Baxter, Carl A.,Cleator, Ed,Brands, Karel M. J.,Edwards, John S.,Reamer, Robert A.,Sheen, Faye J.,Stewart, Gavin W.,Strotman, Neil A.,Wallace, Debra J.. "The first large-scale synthesis of MK-4305: A dual orexin receptor antagonist for the treatment of sleep disorder". . p. 367 - 375. Retrieved 2012/05/19.