[(R)-5-(5-amino-2-fluoro-phenyl)-2,2,5-tris-fluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(R)-5-(5-amino-2-fluoro-phenyl)-2,2,5-tris-fluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester
• CAS No.: 1386986-03-3
• Molecular Formula: C₁₈H₂₃F₄N₃O₃
• Molecular Weight: 405.393

Synonyms:[(R)-5-(5-amino-2-fluoro-phenyl)-2,2,5-tris-fluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester

Chemical Property of [(R)-5-(5-amino-2-fluoro-phenyl)-2,2,5-tris-fluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of [(R)-5-(5-amino-2-fluoro-phenyl)-2,2,5-tris-fluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester

There total 11 articles about [(R)-5-(5-amino-2-fluoro-phenyl)-2,2,5-tris-fluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic 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:

C18H21F4N5O3 (1388840-94-5) → [(R)-5-(5-amino-2-fluoro-phenyl)-2,2,5-tris-fluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester (1386986-03-3)

Guidance literature:

With hydrogen; 5%-palladium/activated carbon; In tetrahydrofuran; ethanol;

Reference yield:

(R)-2-(5-bromo-2-fluoro-phenyl)-2-fluoromethyl-1-(2-nitro-benzenesulfonyl)-aziridine (1386985-95-0) → [(R)-5-(5-amino-2-fluoro-phenyl)-2,2,5-tris-fluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester (1386986-03-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C / Inert atmosphere

1.2: 16 h / 25 °C / Inert atmosphere

2.1: water; lithium hydroxide / tetrahydrofuran; methanol / 0.5 h / 20 °C

3.1: chloroformic acid ethyl ester; 4-methyl-morpholine / dichloromethane / 1 h / 20 °C

4.1: mercaptoacetic acid; potassium carbonate / N,N-dimethyl-formamide / 3 h / 60 °C

5.1: Hexamethyldisiloxane; phosphorous (V) sulfide / toluene / 4 h / 100 °C

6.1: ammonia / methanol / 72 h / 80 °C / Sealed tube

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 40 °C

8.1: sodium azide; copper(l) iodide; sodium L-ascorbate; trans-N,N'-dimethyl-1,2-cyclohexyldiamine / ethanol; water / 70 °C / Inert atmosphere

9.1: hydrogen / 5%-palladium/activated carbon / ethanol; tetrahydrofuran

With 4-methyl-morpholine; trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide; sodium azide; Hexamethyldisiloxane; ammonia; water; hydrogen; phosphorous (V) sulfide; chloroformic acid ethyl ester; sodium hydride; potassium carbonate; mercaptoacetic acid; sodium L-ascorbate; N-ethyl-N,N-diisopropylamine; lithium hydroxide; 5%-palladium/activated carbon; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil;

Reference yield:

C19H17BrF4N2O7S (1386985-98-3) → [(R)-5-(5-amino-2-fluoro-phenyl)-2,2,5-tris-fluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester (1386986-03-3)

Guidance literature:

Multi-step reaction with 7 steps

1: chloroformic acid ethyl ester; 4-methyl-morpholine / dichloromethane / 1 h / 20 °C

2: mercaptoacetic acid; potassium carbonate / N,N-dimethyl-formamide / 3 h / 60 °C

3: Hexamethyldisiloxane; phosphorous (V) sulfide / toluene / 4 h / 100 °C

4: ammonia / methanol / 72 h / 80 °C / Sealed tube

5: N-ethyl-N,N-diisopropylamine / dichloromethane / 40 °C

6: sodium azide; copper(l) iodide; sodium L-ascorbate; trans-N,N'-dimethyl-1,2-cyclohexyldiamine / ethanol; water / 70 °C / Inert atmosphere

7: hydrogen / 5%-palladium/activated carbon / ethanol; tetrahydrofuran

With 4-methyl-morpholine; trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide; sodium azide; Hexamethyldisiloxane; ammonia; hydrogen; phosphorous (V) sulfide; chloroformic acid ethyl ester; potassium carbonate; mercaptoacetic acid; sodium L-ascorbate; N-ethyl-N,N-diisopropylamine; 5%-palladium/activated carbon; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

upstream raw materials:

N-[(R)-1-(5-bromo-2-fluoro-phenyl)-1-fluoromethyl-2-hydroxy-ethyl]-2-nitro-benzenesulfonamide

(R)-2-(5-bromo-2-fluoro-phenyl)-2-fluoromethyl-1-(2-nitro-benzenesulfonyl)-aziridine

2-[(R)-2-(5-bromo-2-fluoro-phenyl)-3-fluoro-2-(2-nitro-benzenesulfonylamino)-propoxy]-3-fluoro-2-fluoromethyl-propionic acid ethyl ester

(R)-5-(5-bromo-2-fluoro-phenyl)-2,2,5-tris-fluoromethyl-4-(2-nitro-benzenesulfonyl)-morpholin-3-one

Downstream raw materials:

5-cyano-3-methyl-pyridine-2-carboxylic acid [3-((R)-5-amino-3,6,6-tris-fluoromethyl-3,6-dihydro-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-amide

((R)-5-{5-[(5-cyano-3-methyl-pyridine-2-carbonyl)-amino]-2-fluoro-phenyl}-2,2,5-tris-fluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl)-carbamicacid tert-butyl ester

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