Boc-(τ-N-methyl)His amide of (3S,4S)-1-<<(3-methylbutyl)carbonyl>amino>-3-hydroxy-4-amino-5-cyclohexylpentane

Base Information

• Chemical Name: Boc-(τ-N-methyl)His amide of (3S,4S)-1-<<(3-methylbutyl)carbonyl>amino>-3-hydroxy-4-amino-5-cyclohexylpentane
• CAS No.: 108868-81-1
• Molecular Formula: C₂₉H₅₁N₅O₅
• Molecular Weight: 549.754

Synonyms:Boc-(τ-N-methyl)His amide of (3S,4S)-1-<<(3-methylbutyl)carbonyl>amino>-3-hydroxy-4-amino-5-cyclohexylpentane

Chemical Property of Boc-(τ-N-methyl)His amide of (3S,4S)-1-<<(3-methylbutyl)carbonyl>amino>-3-hydroxy-4-amino-5-cyclohexylpentane

Chemical Property:

Purity/Quality:

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Technology Process of Boc-(τ-N-methyl)His amide of (3S,4S)-1-<<(3-methylbutyl)carbonyl>amino>-3-hydroxy-4-amino-5-cyclohexylpentane

There total 7 articles about Boc-(τ-N-methyl)His amide of (3S,4S)-1-<<(3-methylbutyl)carbonyl>amino>-3-hydroxy-4-amino-5-cyclohexylpentane 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:

(S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal (98105-42-1) → Boc-(τ-N-methyl)His amide of (3S,4S)-1-<<(3-methylbutyl)carbonyl>amino>-3-hydroxy-4-amino-5-cyclohexylpentane (108868-81-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 15 min

2: 95 percent / H₂, NH₃ / Raney Ni / methanol / 2280 Torr

3: 91 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

4: 4 M aq. HCl / dioxane

5: N-methylmorpholine, 1-hydroxybenzotriazole monohydrate, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / 14 h / -23 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; ammonia; hydrogen; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium diisopropyl amide; nickel; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00390a018

Reference yield:

(2R,3S)-3-(t-butoxycarbonylamino)-4-cyclohexyl-1,2-epoxybutane (107202-61-9) → Boc-(τ-N-methyl)His amide of (3S,4S)-1-<<(3-methylbutyl)carbonyl>amino>-3-hydroxy-4-amino-5-cyclohexylpentane (108868-81-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 65 percent / methanol; H₂O / 18 h / Ambient temperature

2: 95 percent / H₂, NH₃ / Raney Ni / methanol / 2280 Torr

3: 91 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

4: 4 M aq. HCl / dioxane

5: N-methylmorpholine, 1-hydroxybenzotriazole monohydrate, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / 14 h / -23 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; ammonia; hydrogen; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; nickel; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00390a018

Reference yield:

(3S,4S)-3-hydroxy-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanenitrile (108868-54-8) → Boc-(τ-N-methyl)His amide of (3S,4S)-1-<<(3-methylbutyl)carbonyl>amino>-3-hydroxy-4-amino-5-cyclohexylpentane (108868-81-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / H₂, NH₃ / Raney Ni / methanol / 2280 Torr

2: 91 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

3: 4 M aq. HCl / dioxane

4: N-methylmorpholine, 1-hydroxybenzotriazole monohydrate, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / 14 h / -23 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; ammonia; hydrogen; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; nickel; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00390a018

upstream raw materials:

N^α-(tert-butoxycarbony1)- N^τ-methyl-L-histidine

4-methylvaleroyl chloride

(S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal

(2R,3S)-3-(t-butoxycarbonylamino)-4-cyclohexyl-1,2-epoxybutane

Downstream raw materials:

{(S)-1-[(S)-1-[(1S,2S)-1-Cyclohexylmethyl-2-hydroxy-4-(4-methyl-pentanoylamino)-butylcarbamoyl]-2-(1-methyl-1H-imidazol-4-yl)-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

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