N-<(2R)-2-<(tert-butoxycarbonyl)methyl>-6-<(4'-oxobutyl)amino>hexanoyl>-L-phenylalanine N-methylamide

Base Information

Chemical Name:N-<(2R)-2-<(tert-butoxycarbonyl)methyl>-6-<(4'-oxobutyl)amino>hexanoyl>-L-phenylalanine N-methylamide
CAS No.:169270-13-7
Molecular Formula:C₂₆H₄₁N₃O₅
Molecular Weight:475.629
Hs Code.:

Synonyms:N-<(2R)-2-<(tert-butoxycarbonyl)methyl>-6-<(4'-oxobutyl)amino>hexanoyl>-L-phenylalanine N-methylamide

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Chemical Property of N-<(2R)-2-<(tert-butoxycarbonyl)methyl>-6-<(4'-oxobutyl)amino>hexanoyl>-L-phenylalanine N-methylamide

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Technology Process of N-<(2R)-2-<(tert-butoxycarbonyl)methyl>-6-<(4'-oxobutyl)amino>hexanoyl>-L-phenylalanine N-methylamide

There total 13 articles about N-<(2R)-2-<(tert-butoxycarbonyl)methyl>-6-<(4'-oxobutyl)amino>hexanoyl>-L-phenylalanine N-methylamide 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: 63.0%

: 141-75-3
butyryl chloride

: 168974-00-3
N-[(2R)-2-(tert-Butoxycarbonylmethyl)-6-(amino)hexanoyl]-L-phenylalanine N-methylamide

: 169270-13-7
N-<(2R)-2-<(tert-butoxycarbonyl)methyl>-6-<(4'-oxobutyl)amino>hexanoyl>-L-phenylalanine N-methylamide

Guidance literature:: With triethylamine; In N,N-dimethyl-formamide; for 1.5h; Ambient temperature;
DOI:10.1021/jm00014a010

Reference yield:

: 629-11-8
1,6-hexanediol

: 169270-13-7
N-<(2R)-2-<(tert-butoxycarbonyl)methyl>-6-<(4'-oxobutyl)amino>hexanoyl>-L-phenylalanine N-methylamide

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) NaH, 3.) pyridinium dichromate

2: 90 percent / oxalyl chloride, DMF / CH₂Cl₂ / 0 - 20 °C

3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, from -78 deg C to RT

4: 1.) diisopropylamine, n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, from -78 deg C to RT

5: 85 percent / 1,4-cyclohexadiene / 20percent Pd(OH)2/C / ethanol / 65 °C

6: 96 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 °C

7: 80 percent / tetrabutylammonium iodide, NaN₃ / toluene; H₂O / 17 h / 70 °C

8: 90 percent / H₂O₂, LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / Ambient temperature

9: 74 percent / diethylcyanophosphonate, Et₃N / dimethylformamide / 3 h / -10 - 20 °C

10: 90 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 1.2 h / 25 °C / 1551.4 Torr

11: 63 percent / Et₃N / dimethylformamide / 1.5 h / Ambient temperature

With dmap; lithium hydroxide; dipyridinium dichromate; n-butyllithium; sodium azide; oxalyl dichloride; diethyl cyanophosphonate; cyclohexa-1,4-diene; hydrogen; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; diisopropylamine; N,N-dimethyl-formamide; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm00014a010

Reference yield:

: 5292-43-3
bromoacetic acid tert-butyl ester

: 169270-13-7
N-<(2R)-2-<(tert-butoxycarbonyl)methyl>-6-<(4'-oxobutyl)amino>hexanoyl>-L-phenylalanine N-methylamide

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) diisopropylamine, n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, from -78 deg C to RT

2: 85 percent / 1,4-cyclohexadiene / 20percent Pd(OH)2/C / ethanol / 65 °C

3: 96 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 °C

4: 80 percent / tetrabutylammonium iodide, NaN₃ / toluene; H₂O / 17 h / 70 °C

5: 90 percent / H₂O₂, LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / Ambient temperature

6: 74 percent / diethylcyanophosphonate, Et₃N / dimethylformamide / 3 h / -10 - 20 °C

7: 90 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 1.2 h / 25 °C / 1551.4 Torr

8: 63 percent / Et₃N / dimethylformamide / 1.5 h / Ambient temperature

With dmap; lithium hydroxide; n-butyllithium; sodium azide; diethyl cyanophosphonate; cyclohexa-1,4-diene; hydrogen; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; triethylamine; diisopropylamine; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm00014a010