N-(2(R)-hydroxy-1-(S)-indanyl)-2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanamide

Base Information

• Chemical Name: N-(2(R)-hydroxy-1-(S)-indanyl)-2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanamide
• CAS No.: 150323-37-8
• Molecular Formula: C₄₁H₆₄N₄O₆Si
• Molecular Weight: 737.068
• Mol file: 150323-37-8.mol

Synonyms:N-(2(R)-hydroxy-1-(S)-indanyl)-2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanamide

Chemical Property of N-(2(R)-hydroxy-1-(S)-indanyl)-2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-(2(R)-hydroxy-1-(S)-indanyl)-2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanamide

There total 12 articles about N-(2(R)-hydroxy-1-(S)-indanyl)-2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanamide 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:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → N-(2(R)-hydroxy-1-(S)-indanyl)-2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanamide (150323-37-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 96 percent / imidazole / CH₂Cl₂ / 4 h / 0 - 20 °C

2: 1.) LDA / 1.) THF, hexane, 30 min, 2.) THF, hexane, 3 h

3: 97 percent / 49percent aq. HF / acetonitrile / 18 h / Ambient temperature

4: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

5: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h

6: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h

7: imidazole / 1,2-dimethoxy-ethane / 20 h / 0 - 20 °C

8: 92 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et₃N / dimethylformamide / 18 h / 0 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; lithium hydroxide; hydrogen fluoride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;

DOI:10.1021/jm00047a001

Reference yield:

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) → N-(2(R)-hydroxy-1-(S)-indanyl)-2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanamide (150323-37-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 40percent NaOH / dioxane; H₂O / 2.5 h

2: 40percent NaOH / dioxane; H₂O / 14 h

3: 85 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et₃N / dimethylformamide / 18 h

4: 96 percent / H₂ / 10percent Pd/C / methanol / 3 h

5: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h

6: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h

7: imidazole / 1,2-dimethoxy-ethane / 20 h / 0 - 20 °C

8: 92 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et₃N / dimethylformamide / 18 h / 0 - 20 °C

With 1H-imidazole; lithium hydroxide; sodium hydroxide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm00047a001

Reference yield:

(S)-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (848482-93-9) → N-(2(R)-hydroxy-1-(S)-indanyl)-2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanamide (150323-37-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 40percent NaOH / dioxane; H₂O / 14 h

2: 85 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et₃N / dimethylformamide / 18 h

3: 96 percent / H₂ / 10percent Pd/C / methanol / 3 h

4: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h

5: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h

6: imidazole / 1,2-dimethoxy-ethane / 20 h / 0 - 20 °C

7: 92 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et₃N / dimethylformamide / 18 h / 0 - 20 °C

With 1H-imidazole; lithium hydroxide; sodium hydroxide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm00047a001

upstream raw materials:

(5S)-(5-tert-butyldimethylsilyloxymethyl)furan-2(5H)-one

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

dihydro-5(S)-(hydroxymethyl)-3(R)-(phenylmethyl)-3(2H)-furanone

Downstream raw materials:

indinavir

[14C]-N-Dealkyl Indinavir

Refernces