tert-butyl 2-((5-chlorobenzo[d]oxazol-2-yl)(3-oxobutyl)amino)ethylcarbamate

Base Information

• Chemical Name: tert-butyl 2-((5-chlorobenzo[d]oxazol-2-yl)(3-oxobutyl)amino)ethylcarbamate
• CAS No.: 1276666-10-4
• Molecular Formula: C18H24ClN3O4
• Molecular Weight: 381.859
• Mol file: 1276666-10-4.mol

Synonyms:tert-butyl 2-((5-chlorobenzo[d]oxazol-2-yl)(3-oxobutyl)aMino)ethylcarbaMate;[2-[(5-Chloro-benzooxazol-2-yl)(3-oxobutyl)amino]ethyl]carbamic acid tert-butyl ester

Chemical Property of tert-butyl 2-((5-chlorobenzo[d]oxazol-2-yl)(3-oxobutyl)amino)ethylcarbamate

Chemical Property:

• Melting Point: 145-148℃
• PSA: 89.71000
• LogP: 2.71050

Purity/Quality:

98%Min ^*data from raw suppliers

tert-butyl2-((5-chlorobenzo[d]oxazol-2-yl)(3-oxobutyl)amino)ethylcarbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-butyl 2-((5-chlorobenzo[d]oxazol-2-yl)(3-oxobutyl)amino)ethylcarbamate

There total 2 articles about tert-butyl 2-((5-chlorobenzo[d]oxazol-2-yl)(3-oxobutyl)amino)ethylcarbamate 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:

5-chloro-2-mercaptobenzoxazole (22876-19-3) + N-BOC-1,2-diaminoethane (57260-73-8) + methyl vinyl ketone (78-94-4,25038-87-3) → {2-[(5-chlorobenzoxazol-2-yl)-(3-oxo-butyl)amino]ethyl}carbamic acid tert-butyl ester (1276666-10-4)

Guidance literature:

5-chloro-2-mercaptobenzoxazole; With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 25 ℃; for 1.75h; Industry scale;

N-BOC-1,2-diaminoethane; With triethylamine; In dichloromethane; N,N-dimethyl-formamide; at 10 - 20 ℃; for 2.5h;

methyl vinyl ketone; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 10h;

Reference yield:

5-chloro-2-mercaptobenzoxazole (22876-19-3) → {2-[(5-chlorobenzoxazol-2-yl)-(3-oxo-butyl)amino]ethyl}carbamic acid tert-butyl ester (1276666-10-4)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane; water; acetonitrile / 10.08 h / 20 - 40 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 3: Aza-Michael reaction;

DOI:10.1021/op1002853

Reference yield:

{2-[(5-chlorobenzoxazol-2-yl)-(3-oxo-butyl)amino]ethyl}carbamic acid tert-butyl ester (1276666-10-4) → C13H16ClN3O*C18H14O8 (1276666-16-0) + C13H16ClN3O*C18H14O8 (1276666-14-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 5 - 60 °C

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

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

3.2: 22.25 h / 20 °C / Resolution of racemate

With sodium acetate; sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/op1002853

upstream raw materials:

5-chloro-2-mercaptobenzoxazole

N-BOC-1,2-diaminoethane

methyl vinyl ketone

Downstream raw materials:

C₁₃H₁₆ClN₃O*C₁₈H₁₄O₈

C₁₃H₁₆ClN₃O*C₁₈H₁₄O₈

Suvorexant

Refernces

• 1、 -. "A su Wolei lives is an important intermediate for preparing method (by machine translation)". . . Retrieved 2017/07/12.
• 2、 -. "Process for the preparation of an intermediate for an orexin receptor antagonist". Page/Page column 9; 10. . Retrieved 2017/02/02.