N-((R)-1-((2S,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)acetamide

Base Information

Chemical Name:N-((R)-1-((2S,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)acetamide
CAS No.:906536-51-4
Molecular Formula:C₂₉H₃₃N₅O₃
Molecular Weight:499.613
Hs Code.:

Synonyms:N-((R)-1-((2S,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)acetamide

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Chemical Property of N-((R)-1-((2S,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)acetamide

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Technology Process of N-((R)-1-((2S,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)acetamide

There total 14 articles about N-((R)-1-((2S,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)acetamide 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: 88.0%

: 474023-61-5
(R)-2-amino-1-((2S,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-3-phenylpropan-1-one

: 64-19-7,77671-22-8
acetic acid

: 906536-51-4
N-((R)-1-((2S,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)acetamide

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

Reference yield:

: 474023-59-1
(2S,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidine

: 906536-51-4
N-((R)-1-((2S,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)acetamide

Guidance literature:: Multi-step reaction with 3 steps

1: 75 percent / HOAt; 4-methylmorpholine; ethyldimethylaminopropyl carbodiimide / dimethylformamide / 1.25 h

2: aq. TFA / CH₂Cl₂ / 1 h

3: 88 percent / 1H-benzotriazole; 4-methylmorpholine; ethyldimethylaminopropyl carbodiimide / dimethylformamide; H₂O / 1 h

With 4-methyl-morpholine; 1,2,3-Benzotriazole; 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm060384p

Reference yield:

: tert-butyl (4R)-2-allyl-4-(naphthalen-2-ylmethoxy)pyrrolidine-1-carboxylate

: 906536-51-4
N-((R)-1-((2S,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl)acetamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: BH₃-THF / tetrahydrofuran / 0.5 h

1.2: 25 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 2 h

2.1: Et₃N / CH₂Cl₂ / 0.75 h / 20 °C

3.1: 584 mg / NaN₃ / dimethylsulfoxide / 3 h / 70 °C

4.1: aq. TFA / CH₂Cl₂ / 1 h

5.1: 75 percent / HOAt; 4-methylmorpholine; ethyldimethylaminopropyl carbodiimide / dimethylformamide / 1.25 h

6.1: aq. TFA / CH₂Cl₂ / 1 h

7.1: 88 percent / 1H-benzotriazole; 4-methylmorpholine; ethyldimethylaminopropyl carbodiimide / dimethylformamide; H₂O / 1 h

With 4-methyl-morpholine; 1,2,3-Benzotriazole; sodium azide; 1-hydroxy-7-aza-benzotriazole; borane-THF; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jm060384p