(2R,4S,5S)-5-Amino-6-[3-(4,4-dimethyl-pentyl)-phenyl]-4-hydroxy-2-methyl-hexanoic acid butylamide

Base Information

• Chemical Name: (2R,4S,5S)-5-Amino-6-[3-(4,4-dimethyl-pentyl)-phenyl]-4-hydroxy-2-methyl-hexanoic acid butylamide
• CAS No.: 181716-45-0
• Molecular Formula: C₂₄H₄₂N₂O₂
• Molecular Weight: 390.61

Synonyms:(2R,4S,5S)-5-Amino-6-[3-(4,4-dimethyl-pentyl)-phenyl]-4-hydroxy-2-methyl-hexanoic acid butylamide

Chemical Property of (2R,4S,5S)-5-Amino-6-[3-(4,4-dimethyl-pentyl)-phenyl]-4-hydroxy-2-methyl-hexanoic acid butylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (2R,4S,5S)-5-Amino-6-[3-(4,4-dimethyl-pentyl)-phenyl]-4-hydroxy-2-methyl-hexanoic acid butylamide

There total 16 articles about (2R,4S,5S)-5-Amino-6-[3-(4,4-dimethyl-pentyl)-phenyl]-4-hydroxy-2-methyl-hexanoic acid butylamide 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: 70.0%

(4S,5S)-5-((R)-2-Butylcarbamoyl-propyl)-4-[3-(4,4-dimethyl-pentyl)-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (181716-99-4) → (2R,4S,5S)-5-Amino-6-[3-(4,4-dimethyl-pentyl)-phenyl]-4-hydroxy-2-methyl-hexanoic acid butylamide (181716-45-0)

Guidance literature:

With trifluoroacetic acid; In water; for 1h; Ambient temperature;

DOI:10.1016/S0960-894X(96)00279-X

Reference yield:

1,3-dimethanol benzene (626-18-6) → (2R,4S,5S)-5-Amino-6-[3-(4,4-dimethyl-pentyl)-phenyl]-4-hydroxy-2-methyl-hexanoic acid butylamide (181716-45-0)

Guidance literature:

Multi-step reaction with 18 steps

1: 50 percent / imidazole / CH₂Cl₂

2: 90 percent / MnO₂ / CHCl₃ / Heating

3: 81 percent / n-BuLi / tetrahydrofuran

4: TBAF / tetrahydrofuran

5: H₂ / Pd/C

6: 88 percent / NBS, PPh₃ / CH₂Cl₂ / Ambient temperature

7: 1.) n-BuLi, 2.) HCl, H₂O / 1.) THF, 2.) MeCN

8: NaOH / H₂O; dioxane

9: NaOH / H₂O

10: HNMeOMe, NMM

11: LiAlH₄ / diethyl ether

12: Mg / diethyl ether / 0 °C

13: 73 percent / Ambient temperature

14: 81 percent / H₂ / Pd/C

15: 81 percent / PDC / dimethylformamide / 12 h / Ambient temperature

16: NMM / tetrahydrofuran / -20 °C

17: NMM / tetrahydrofuran / 1 h / Ambient temperature

18: 70 percent / TFA / H₂O / 1 h / Ambient temperature

With 4-methyl-morpholine; 1H-imidazole; hydrogenchloride; manganese(IV) oxide; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; tetrabutyl ammonium fluoride; water; hydrogen; magnesium; triphenylphosphine; trifluoroacetic acid; N,0-dimethylhydroxylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(96)00279-X

Reference yield:

[3-(4,4-Dimethyl-pentyl)-phenyl]-methanol (181716-92-7) → (2R,4S,5S)-5-Amino-6-[3-(4,4-dimethyl-pentyl)-phenyl]-4-hydroxy-2-methyl-hexanoic acid butylamide (181716-45-0)

Guidance literature:

Multi-step reaction with 13 steps

1: 88 percent / NBS, PPh₃ / CH₂Cl₂ / Ambient temperature

2: 1.) n-BuLi, 2.) HCl, H₂O / 1.) THF, 2.) MeCN

3: NaOH / H₂O; dioxane

4: NaOH / H₂O

5: HNMeOMe, NMM

6: LiAlH₄ / diethyl ether

7: Mg / diethyl ether / 0 °C

8: 73 percent / Ambient temperature

9: 81 percent / H₂ / Pd/C

10: 81 percent / PDC / dimethylformamide / 12 h / Ambient temperature

11: NMM / tetrahydrofuran / -20 °C

12: NMM / tetrahydrofuran / 1 h / Ambient temperature

13: 70 percent / TFA / H₂O / 1 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; water; hydrogen; magnesium; triphenylphosphine; trifluoroacetic acid; N,0-dimethylhydroxylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(96)00279-X

upstream raw materials:

(4S,5S)-5-((R)-2-Butylcarbamoyl-propyl)-4-[3-(4,4-dimethyl-pentyl)-benzyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

1,3-dimethanol benzene

[3-(4,4-Dimethyl-pentyl)-phenyl]-methanol

1-Bromomethyl-3-(4,4-dimethyl-pentyl)-benzene

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