N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline N'-methylamide

Base Information

Chemical Name:N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline N'-methylamide
CAS No.:224951-72-8
Molecular Formula:C₂₄H₃₇N₃O₄
Molecular Weight:431.575
Hs Code.:

Synonyms:N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline N'-methylamide

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Chemical Property of N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline N'-methylamide

Chemical Property:

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Technology Process of N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline N'-methylamide

There total 6 articles about N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline 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: 49.0%

: 593-51-1
methylamine hydrochloride

: 224951-66-0
N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline

: 224951-72-8
N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline N'-methylamide

Guidance literature:: With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In acetonitrile; for 18h; Ambient temperature;
DOI:10.1021/jo990294a

Reference yield:

: 13734-34-4
N-tert-butoxycarbonyl-L-phenylalanine

: (2S,5R)-5-tert-butylproline N'-methylamide hydrochloride

: 224951-72-8
N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline N'-methylamide

Guidance literature:: With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 19h;
DOI:10.1021/ja012442w

Reference yield:

: 185142-15-8
(2S,5R)-N-(tert-butyloxycarbonyl)-5-tert-butylproline

: 224951-72-8
N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline N'-methylamide

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / DIEA / CH₂Cl₂ / 18 h / Heating

2: 99 percent / HCl gas / CH₂Cl₂ / 2 h / Ambient temperature

3: 94 percent / DIEA, BOP-Cl / CH₂Cl₂ / 18 h / Ambient temperature

4: 64 percent / morpholine / Pd(PPh₃)4 / tetrahydrofuran / 3 h / Ambient temperature

5: 49 percent / DIEA, TBTU / acetonitrile / 18 h / Ambient temperature

With morpholine; hydrogenchloride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jo990294a