tert-butyl (R)-1-((2R,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate

Base Information

• Chemical Name: tert-butyl (R)-1-((2R,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate
• CAS No.: 906537-32-4
• Molecular Formula: C₃₂H₃₉N₅O₄
• Molecular Weight: 557.693
• Mol file: 906537-32-4.mol

Synonyms:tert-butyl (R)-1-((2R,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate

Chemical Property of tert-butyl (R)-1-((2R,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (R)-1-((2R,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate

There total 5 articles about tert-butyl (R)-1-((2R,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate 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:

tert-butyl (4R)-2-allyl-4-(naphthalen-2-ylmethoxy)pyrrolidine-1-carboxylate → tert-butyl (R)-1-((2R,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate (906537-32-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: BH₃-THF / tetrahydrofuran / 0.5 h

1.2: 33 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 2 h

2.1: Et₃N / CH₂Cl₂ / 0.75 h / 20 °C

3.1: NaN₃ / dimethylsulfoxide / 3 h / 70 °C

4.1: aq. TFA / CH₂Cl₂ / 1 h

5.1: HOAt; 4-methylmorpholine; ethyldimethylaminopropyl carbodiimide / dimethylformamide / 1.25 h

With 4-methyl-morpholine; sodium azide; 1-hydroxy-7-aza-benzotriazole; borane-THF; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jm060384p

Reference yield:

tert-butyl (2R,4R)-2-(3-hydroxypropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidine-1-carboxylate (906536-41-2) → tert-butyl (R)-1-((2R,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate (906537-32-4)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N / CH₂Cl₂ / 0.75 h / 20 °C

2: NaN₃ / dimethylsulfoxide / 3 h / 70 °C

3: aq. TFA / CH₂Cl₂ / 1 h

4: HOAt; 4-methylmorpholine; ethyldimethylaminopropyl carbodiimide / dimethylformamide / 1.25 h

With 4-methyl-morpholine; sodium azide; 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jm060384p

Reference yield:

tert-butyl (2R,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidine-1-carboxylate (906536-42-3) → tert-butyl (R)-1-((2R,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate (906537-32-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. TFA / CH₂Cl₂ / 1 h

2: HOAt; 4-methylmorpholine; ethyldimethylaminopropyl carbodiimide / dimethylformamide / 1.25 h

With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm060384p

upstream raw materials:

(2R,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidine

Boc-D-Phe-OH

tert-butyl (2R,4R)-2-(3-hydroxypropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidine-1-carboxylate

tert-butyl (2R,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidine-1-carboxylate

Downstream raw materials:

(R)-2-amino-1-((2R,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-3-phenylpropan-1-one

(S)-2-acetamido-N₁-((R)-1-((2R,4R)-2-(3-aminopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)pentanediamide

(S)-2-acetamido-N₁-((R)-1-((2R,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)pentanediamide

(S)-tert-butyl 2-((R)-1-((2R,4R)-2-(3-aminopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamoyl)piperidine-1-carboxylate