5-[4-(3-prop-2-ynylcarbamoyl-propionylamino)-phenyl]-isoxazole-3-carboxylic acid methyl ester

Base Information

Chemical Name:5-[4-(3-prop-2-ynylcarbamoyl-propionylamino)-phenyl]-isoxazole-3-carboxylic acid methyl ester
CAS No.:879216-20-3
Molecular Formula:C₁₈H₁₇N₃O₅
Molecular Weight:355.35
Hs Code.:

Synonyms:5-[4-(3-prop-2-ynylcarbamoyl-propionylamino)-phenyl]-isoxazole-3-carboxylic acid methyl ester

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Chemical Property of 5-[4-(3-prop-2-ynylcarbamoyl-propionylamino)-phenyl]-isoxazole-3-carboxylic acid methyl ester

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Technology Process of 5-[4-(3-prop-2-ynylcarbamoyl-propionylamino)-phenyl]-isoxazole-3-carboxylic acid methyl ester

There total 5 articles about 5-[4-(3-prop-2-ynylcarbamoyl-propionylamino)-phenyl]-isoxazole-3-carboxylic acid methyl 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: 74.0%

: 5-[4-(3-carboxy-propionylamino)-phenyl]-isoxazole-3-carboxylic acid methyl ester

: 2450-71-7
Propargylamine

: 879216-20-3
5-[4-(3-prop-2-ynylcarbamoyl-propionylamino)-phenyl]-isoxazole-3-carboxylic acid methyl ester

Guidance literature:: 5-[4-(3-carboxy-propionylamino)-phenyl]-isoxazole-3-carboxylic acid methyl ester; With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 0.5h;

Propargylamine; In N,N-dimethyl-formamide; for 8h;
DOI:10.1021/ol052895w

Reference yield:

: 487034-01-5
5-(4-nitro-phenyl)-isoxazole-3-carboxylic acid methyl ester

: 879216-20-3
5-[4-(3-prop-2-ynylcarbamoyl-propionylamino)-phenyl]-isoxazole-3-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 91 percent / glacial acetic acid; hydrogen / Pd/C / 4 h

2.1: 91 percent / HATU; 2,4,6-collidine / dimethylformamide / 3 h

3.1: TFA / CH₂Cl₂ / 0.5 h

4.1: EDC; HOBt; DIEA / dimethylformamide / 0.5 h

4.2: 74 percent / dimethylformamide / 8 h

With 2,4,6-trimethyl-pyridine; hydrogen; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol052895w

Reference yield:

: 100-19-6
(4-nitrophenyl)ethanone

: 879216-20-3
5-[4-(3-prop-2-ynylcarbamoyl-propionylamino)-phenyl]-isoxazole-3-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaOMe / methanol / 12 h / Heating

1.2: 36 percent / NH₂OH*HCl; p-TsOH*H₂O / methanol / 72 h / Heating

2.1: 91 percent / glacial acetic acid; hydrogen / Pd/C / 4 h

3.1: 91 percent / HATU; 2,4,6-collidine / dimethylformamide / 3 h

4.1: TFA / CH₂Cl₂ / 0.5 h

5.1: EDC; HOBt; DIEA / dimethylformamide / 0.5 h

5.2: 74 percent / dimethylformamide / 8 h

With 2,4,6-trimethyl-pyridine; hydrogen; sodium methylate; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol052895w