[2-(4-{3-[4-(5-cyclopentylmethyl-[1,2,4]oxadiazol-3-yl)-3-fluoro-phenoxy]-propyl}-[1,4]diazepan-1-yl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [2-(4-{3-[4-(5-cyclopentylmethyl-[1,2,4]oxadiazol-3-yl)-3-fluoro-phenoxy]-propyl}-[1,4]diazepan-1-yl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester
• CAS No.: 360553-99-7
• Molecular Formula: C₃₀H₄₄FN₅O₅
• Molecular Weight: 573.708

Synonyms:[2-(4-{3-[4-(5-cyclopentylmethyl-[1,2,4]oxadiazol-3-yl)-3-fluoro-phenoxy]-propyl}-[1,4]diazepan-1-yl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester

Chemical Property of [2-(4-{3-[4-(5-cyclopentylmethyl-[1,2,4]oxadiazol-3-yl)-3-fluoro-phenoxy]-propyl}-[1,4]diazepan-1-yl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester

Chemical Property:

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Technology Process of [2-(4-{3-[4-(5-cyclopentylmethyl-[1,2,4]oxadiazol-3-yl)-3-fluoro-phenoxy]-propyl}-[1,4]diazepan-1-yl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester

There total 6 articles about [2-(4-{3-[4-(5-cyclopentylmethyl-[1,2,4]oxadiazol-3-yl)-3-fluoro-phenoxy]-propyl}-[1,4]diazepan-1-yl)-1-methyl-2-oxo-ethyl]-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:

Boc-(R)-Ala (3744-87-4,7764-95-6,15761-38-3) + 1-(3-{4-[5-(cyclopentylmethyl)-1,2,4-oxadiazol-3-yl]-3-fluorophenoxy}propyl)-1,4-diazepane (360553-62-4) → [2-(4-{3-[4-(5-cyclopentylmethyl-[1,2,4]oxadiazol-3-yl)-3-fluoro-phenoxy]-propyl}-[1,4]diazepan-1-yl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester (360553-99-7)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.bmcl.2003.11.038

Reference yield:

2-fluoro-4-hydroxybenzonitrile (82380-18-5) → [2-(4-{3-[4-(5-cyclopentylmethyl-[1,2,4]oxadiazol-3-yl)-3-fluoro-phenoxy]-propyl}-[1,4]diazepan-1-yl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester (360553-99-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / K₂CO₃ / butan-2-one / Heating

2: K₂CO₃; KI / butan-2-one / Heating

3: H₂NOH*HCl; K₂CO₃ / ethanol / Heating

4: Et₃N / acetone / 20 °C

5: toluene / Heating

6: 98 percent / TFA / CH₂Cl₂ / 20 °C

7: iPr₂NEt; DMAP; EDCI / CH₂Cl₂ / 0 - 20 °C

With dmap; hydroxylamine hydrochloride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; potassium iodide; In ethanol; dichloromethane; acetone; toluene; butanone;

DOI:10.1016/j.bmcl.2003.11.038

Reference yield:

4-(3-chloropropoxy)-2-fluorobenzonitrile (873547-02-5) → [2-(4-{3-[4-(5-cyclopentylmethyl-[1,2,4]oxadiazol-3-yl)-3-fluoro-phenoxy]-propyl}-[1,4]diazepan-1-yl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester (360553-99-7)

Guidance literature:

Multi-step reaction with 6 steps

1: K₂CO₃; KI / butan-2-one / Heating

2: H₂NOH*HCl; K₂CO₃ / ethanol / Heating

3: Et₃N / acetone / 20 °C

4: toluene / Heating

5: 98 percent / TFA / CH₂Cl₂ / 20 °C

6: iPr₂NEt; DMAP; EDCI / CH₂Cl₂ / 0 - 20 °C

With dmap; hydroxylamine hydrochloride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; potassium iodide; In ethanol; dichloromethane; acetone; toluene; butanone;

DOI:10.1016/j.bmcl.2003.11.038

upstream raw materials:

Boc-(R)-Ala

1-(3-{4-[5-(cyclopentylmethyl)-1,2,4-oxadiazol-3-yl]-3-fluorophenoxy}propyl)-1,4-diazepane

2-fluoro-4-hydroxybenzonitrile

4-(3-chloropropoxy)-2-fluorobenzonitrile

Downstream raw materials:

(2R)-1-[4-(3-{4-[5-(cyclopentylmethyl)-1,2,4-oxadiazol-3-yl]-3-fluorophenoxy}propyl)-1,4-diazepan-1-yl]-1-oxo-2-propanamine

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