(R)-2-{4-[3-(3-cyano-phenyl)-ureido]-3-fluoro-phenyl}-morpholine-4-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(R)-2-{4-[3-(3-cyano-phenyl)-ureido]-3-fluoro-phenyl}-morpholine-4-carboxylic acid tert-butyl ester
CAS No.:1415757-41-3
Molecular Formula:C₂₃H₂₅FN₄O₄
Molecular Weight:440.474
Hs Code.:

Synonyms:(R)-2-{4-[3-(3-cyano-phenyl)-ureido]-3-fluoro-phenyl}-morpholine-4-carboxylic acid tert-butyl ester

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Chemical Property of (R)-2-{4-[3-(3-cyano-phenyl)-ureido]-3-fluoro-phenyl}-morpholine-4-carboxylic acid tert-butyl ester

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Technology Process of (R)-2-{4-[3-(3-cyano-phenyl)-ureido]-3-fluoro-phenyl}-morpholine-4-carboxylic acid tert-butyl ester

There total 8 articles about (R)-2-{4-[3-(3-cyano-phenyl)-ureido]-3-fluoro-phenyl}-morpholine-4-carboxylic acid tert-butyl 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: 100.0%

: 32315-10-9
bis(trichloromethyl) carbonate

: 1400997-47-8
(+)-(R)-2-(4-amino-3-fluorophenyl)-morpholine-4-carboxylic acid tert-butyl ester

: 2237-30-1
m-cyanoaniline

: 1415757-41-3
(R)-2-{4-[3-(3-cyano-phenyl)-ureido]-3-fluoro-phenyl}-morpholine-4-carboxylic acid tert-butyl ester

Guidance literature:: bis(trichloromethyl) carbonate; (+)-(R)-2-(4-amino-3-fluorophenyl)-morpholine-4-carboxylic acid tert-butyl ester; With sodium carbonate; In dichloromethane; water; at 20 ℃; for 2.5h;

m-cyanoaniline; In dichloromethane; water; at 20 ℃; for 2h;

Reference yield:

: 1260857-14-4
2-chloro-1-(4-bromo-3-fluorophenyl)-ethanone

: 1415757-41-3
(R)-2-{4-[3-(3-cyano-phenyl)-ureido]-3-fluoro-phenyl}-morpholine-4-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: ethanol; sodium tetrahydroborate / 1.08 h / 5 - 20 °C

1.2: 20 - 40 °C

2.1: tetrahydrofuran / 20 °C

3.1: dichloromethane / 20 °C

4.1: triethylamine; methanesulfonyl chloride / tetrahydrofuran / 0.5 h / 0 - 20 °C

4.2: 1 h / 0 - 20 °C

5.1: sodium t-butanolate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / toluene / 1 h / 100 °C / Inert atmosphere

6.1: ammonium formate / palladium 10% on activated carbon / methanol / 1 h / 60 °C / Inert atmosphere

7.1: Chiralpak AD / isopropyl alcohol; n-heptane / 13501.4 Torr / Resolution of racemate

8.1: sodium carbonate / dichloromethane; water / 2.5 h / 20 °C

8.2: 2 h / 20 °C

With sodium tetrahydroborate; ethanol; ammonium formate; sodium carbonate; methanesulfonyl chloride; triethylamine; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium 10% on activated carbon; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; In tetrahydrofuran; methanol; n-heptane; dichloromethane; water; isopropyl alcohol; toluene;

Reference yield:

: 695188-21-7
4-bromo-3-fluorobenzoyl chloride

: 1415757-41-3
(R)-2-{4-[3-(3-cyano-phenyl)-ureido]-3-fluoro-phenyl}-morpholine-4-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: diethyl ether; acetonitrile; tetrahydrofuran / 0.5 h / 0 - 20 °C

1.2: 0.5 h / 0 - 20 °C

2.1: ethanol; sodium tetrahydroborate / 1.08 h / 5 - 20 °C

2.2: 20 - 40 °C

3.1: tetrahydrofuran / 20 °C

4.1: dichloromethane / 20 °C

5.1: triethylamine; methanesulfonyl chloride / tetrahydrofuran / 0.5 h / 0 - 20 °C

5.2: 1 h / 0 - 20 °C

6.1: sodium t-butanolate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / toluene / 1 h / 100 °C / Inert atmosphere

7.1: ammonium formate / palladium 10% on activated carbon / methanol / 1 h / 60 °C / Inert atmosphere

8.1: Chiralpak AD / isopropyl alcohol; n-heptane / 13501.4 Torr / Resolution of racemate

9.1: sodium carbonate / dichloromethane; water / 2.5 h / 20 °C

9.2: 2 h / 20 °C

With sodium tetrahydroborate; ethanol; ammonium formate; sodium carbonate; methanesulfonyl chloride; triethylamine; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium 10% on activated carbon; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; In tetrahydrofuran; methanol; diethyl ether; n-heptane; dichloromethane; water; isopropyl alcohol; toluene; acetonitrile;