N-[5-(3-carbomethoxyphenyl)-1(S)-cyanopentyl]-3-methyl-Nα-(tert-butoxycarbonyl)-L-phenylalaninamide

Base Information

Chemical Name:N-[5-(3-carbomethoxyphenyl)-1(S)-cyanopentyl]-3-methyl-Nα-(tert-butoxycarbonyl)-L-phenylalaninamide
CAS No.:389600-29-7
Molecular Formula:C₂₈H₃₅N₃O₅
Molecular Weight:493.603
Hs Code.:

Synonyms:N-[5-(3-carbomethoxyphenyl)-1(S)-cyanopentyl]-3-methyl-Nα-(tert-butoxycarbonyl)-L-phenylalaninamide

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Chemical Property of N-[5-(3-carbomethoxyphenyl)-1(S)-cyanopentyl]-3-methyl-Nα-(tert-butoxycarbonyl)-L-phenylalaninamide

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Technology Process of N-[5-(3-carbomethoxyphenyl)-1(S)-cyanopentyl]-3-methyl-Nα-(tert-butoxycarbonyl)-L-phenylalaninamide

There total 13 articles about N-[5-(3-carbomethoxyphenyl)-1(S)-cyanopentyl]-3-methyl-Nα-(tert-butoxycarbonyl)-L-phenylalaninamide 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:

: 3-[4-(2-tert-butoxycarbonylamino-3-m-tolyl-propionylamino)-4-carbamoyl-butyl]-benzoic acid methyl ester

: 389600-29-7
N-[5-(3-carbomethoxyphenyl)-1(S)-cyanopentyl]-3-methyl-Nα-(tert-butoxycarbonyl)-L-phenylalaninamide

Guidance literature:: With pyridine; oxalyl dichloride; In N,N-dimethyl-formamide; at 0 ℃; for 1.5h;
DOI:10.1021/jm010206q

Reference yield:

: 618-89-3
methyl 3-bromobenzoate

: 389600-29-7
N-[5-(3-carbomethoxyphenyl)-1(S)-cyanopentyl]-3-methyl-Nα-(tert-butoxycarbonyl)-L-phenylalaninamide

Guidance literature:: Multi-step reaction with 8 steps

1: 56 percent / (Ph₃P)2PdCl₂; Et₃N / 2 h / Heating

2: 39.4 percent / Alcalase 2.4L; aq. NaHCO₃ / acetonitrile / 2.5 h / 20 °C

3: 99 percent / H₂ / 10percent Pd/C / ethanol; tetrahydrofuran / 760.05 Torr

4: N-methylmorpholine / CH₂Cl₂ / 0.17 h / -10 °C

5: 17.6 g / NH₃(g) / CH₂Cl₂ / 2 h / -10 - 20 °C

6: HCl(g) / ethyl acetate

7: N-methylmorpholine; HOAt; EDCI / CH₂Cl₂ / 20 °C

8: oxalyl chloride; pyridine / dimethylformamide / 1.5 h / 0 °C

With 4-methyl-morpholine; pyridine; hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; 1-hydroxy-7-aza-benzotriazole; oxalyl dichloride; alcalase 2.4L; ammonia; hydrogen; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 10percent Pd/C; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm010206q

Reference yield:

: 71460-02-1,173306-82-6
methyl 2-[((1,1-dimethylethoxy)carbonyl)amino]-4-pentynoate

: 389600-29-7
N-[5-(3-carbomethoxyphenyl)-1(S)-cyanopentyl]-3-methyl-Nα-(tert-butoxycarbonyl)-L-phenylalaninamide

Guidance literature:: Multi-step reaction with 8 steps

1: 56 percent / (Ph₃P)2PdCl₂; Et₃N / 2 h / Heating

2: 39.4 percent / Alcalase 2.4L; aq. NaHCO₃ / acetonitrile / 2.5 h / 20 °C

3: 99 percent / H₂ / 10percent Pd/C / ethanol; tetrahydrofuran / 760.05 Torr

4: N-methylmorpholine / CH₂Cl₂ / 0.17 h / -10 °C

5: 17.6 g / NH₃(g) / CH₂Cl₂ / 2 h / -10 - 20 °C

6: HCl(g) / ethyl acetate

7: N-methylmorpholine; HOAt; EDCI / CH₂Cl₂ / 20 °C

8: oxalyl chloride; pyridine / dimethylformamide / 1.5 h / 0 °C

With 4-methyl-morpholine; pyridine; hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; 1-hydroxy-7-aza-benzotriazole; oxalyl dichloride; alcalase 2.4L; ammonia; hydrogen; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 10percent Pd/C; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm010206q