tert-butyl (R)-1-((2S,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-((2S,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate
CAS No.:474023-60-4
Molecular Formula:C₃₂H₃₉N₅O₄
Molecular Weight:557.693
Hs Code.:

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

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

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

There total 12 articles about tert-butyl (R)-1-((2S,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: 75.0%

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

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

: 474023-60-4
tert-butyl (R)-1-((2S,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate

Guidance literature:: With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; for 1.25h;
DOI:10.1021/jm060384p

Reference yield:

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

: 474023-60-4
tert-butyl (R)-1-((2S,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate

Guidance literature:: Multi-step reaction with 5 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

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:

: 906536-17-2,630425-40-0
(2R,4R)-1-(tert-butoxycarbonyl)-4-(naphthalen-2-ylmethoxy)pyrrolidine-2-carboxylic acid

: 474023-60-4
tert-butyl (R)-1-((2S,4R)-2-(3-azidopropyl)-4-(naphthalen-2-ylmethoxy)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate

Guidance literature:: Multi-step reaction with 9 steps

1: 56 percent / DMAP; ethyldimethylaminopropyl carbodiimide / CH₂Cl₂ / 20 °C

2: 74 percent / NaBH₄; AcOH / CH₂Cl₂

3: toluene / 15 h / 100 °C

4: 246 mg / toluene / 20 h / Heating

5: 56 percent / LiAlH₄ / tetrahydrofuran / 0 °C

6: Et₃N / CH₂Cl₂ / 0.75 h / 20 °C

7: 584 mg / NaN₃ / dimethylsulfoxide / 3 h / 70 °C

8: aq. TFA / CH₂Cl₂ / 1 h

9: 75 percent / HOAt; 4-methylmorpholine; ethyldimethylaminopropyl carbodiimide / dimethylformamide / 1.25 h

With 4-methyl-morpholine; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; 1-hydroxy-7-aza-benzotriazole; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm060384p