N-(tert-butoxycarbonyl)-D-phenylalanyl-(4R)-N-({[(benzyloxy)carbonyl]amino}ethyl)-4-(2-naphthylmethoxy)-D-prolinamide

Base Information

Chemical Name:N-(tert-butoxycarbonyl)-D-phenylalanyl-(4R)-N-({[(benzyloxy)carbonyl]amino}ethyl)-4-(2-naphthylmethoxy)-D-prolinamide
CAS No.:906536-20-7
Molecular Formula:C₄₀H₄₆N₄O₇
Molecular Weight:694.828
Hs Code.:

Synonyms:N-(tert-butoxycarbonyl)-D-phenylalanyl-(4R)-N-({[(benzyloxy)carbonyl]amino}ethyl)-4-(2-naphthylmethoxy)-D-prolinamide

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Chemical Property of N-(tert-butoxycarbonyl)-D-phenylalanyl-(4R)-N-({[(benzyloxy)carbonyl]amino}ethyl)-4-(2-naphthylmethoxy)-D-prolinamide

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Technology Process of N-(tert-butoxycarbonyl)-D-phenylalanyl-(4R)-N-({[(benzyloxy)carbonyl]amino}ethyl)-4-(2-naphthylmethoxy)-D-prolinamide

There total 1 articles about N-(tert-butoxycarbonyl)-D-phenylalanyl-(4R)-N-({[(benzyloxy)carbonyl]amino}ethyl)-4-(2-naphthylmethoxy)-D-prolinamide 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:

: benzyl 2-((2R,4R)-4-(naphthalen-2-ylmethoxy)pyrrolidine-2-carboxamido)ethylcarbamate trifluoroacetate

: 18942-49-9
Boc-D-Phe-OH

: 906536-20-7
N-(tert-butoxycarbonyl)-D-phenylalanyl-(4R)-N-({[(benzyloxy)carbonyl]amino}ethyl)-4-(2-naphthylmethoxy)-D-prolinamide

Guidance literature:: With 4-methyl-morpholine; 1,2,3-Benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; for 3h;
DOI:10.1021/jm060384p

Reference yield: 100.0%

: 906536-20-7
N-(tert-butoxycarbonyl)-D-phenylalanyl-(4R)-N-({[(benzyloxy)carbonyl]amino}ethyl)-4-(2-naphthylmethoxy)-D-prolinamide

: 906536-21-8
benzyl 2-((2R,4R)-1-((R)-2-amino-3-phenylpropanoyl)-4-(naphthalen-2-ylmethoxy)pyrrolidine-2-carboxamido)ethylcarbamate

Guidance literature:: With trifluoroacetic acid; In dichloromethane; for 3h;
DOI:10.1021/jm060384p

Reference yield:

: 906536-20-7
N-(tert-butoxycarbonyl)-D-phenylalanyl-(4R)-N-({[(benzyloxy)carbonyl]amino}ethyl)-4-(2-naphthylmethoxy)-D-prolinamide

: tert-butyl (S)-1-((R)-1-((2R,4R)-2-(2-aminoethylcarbamoyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-ylamino)-1-oxo-3-(1-trityl-1H-imidazol-4-yl)propan-2-ylcarbamate

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / TFA / CH₂Cl₂ / 3 h

2: 69 percent / 1H-benzotriazole; 4-methylmorpholine; ethyldimethylaminopropyl carbodiimide / dimethylformamide / 3 h

3: H₂; pyridine / Pd/C / methanol / 3 h

With 4-methyl-morpholine; pyridine; 1,2,3-Benzotriazole; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm060384p