N₁-(1,1,3,3-tetramethylbutyl)-(3S)-3-[(2S)-2-amino-3-cyclohexylpropanoyl]amino-4-(benzyloxy)-2-hydroxybutanamide

Base Information

• Chemical Name: N₁-(1,1,3,3-tetramethylbutyl)-(3S)-3-[(2S)-2-amino-3-cyclohexylpropanoyl]amino-4-(benzyloxy)-2-hydroxybutanamide
• CAS No.: 1309974-55-7
• Molecular Formula: C₂₈H₄₇N₃O₄
• Molecular Weight: 489.699

Synonyms:N₁-(1,1,3,3-tetramethylbutyl)-(3S)-3-[(2S)-2-amino-3-cyclohexylpropanoyl]amino-4-(benzyloxy)-2-hydroxybutanamide

Chemical Property of N₁-(1,1,3,3-tetramethylbutyl)-(3S)-3-[(2S)-2-amino-3-cyclohexylpropanoyl]amino-4-(benzyloxy)-2-hydroxybutanamide

Chemical Property:

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Technology Process of N₁-(1,1,3,3-tetramethylbutyl)-(3S)-3-[(2S)-2-amino-3-cyclohexylpropanoyl]amino-4-(benzyloxy)-2-hydroxybutanamide

There total 5 articles about N₁-(1,1,3,3-tetramethylbutyl)-(3S)-3-[(2S)-2-amino-3-cyclohexylpropanoyl]amino-4-(benzyloxy)-2-hydroxybutanamide 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:

3-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-1-[(1,1,3,3-tetramethylbutyl)amino]carbonylpropyl (2S)-2-[(tert-butoxycarbonyl)cyclohexyl]propanoate (1309974-53-5) → N1-(1,1,3,3-tetramethylbutyl)-(3S)-3-[(2S)-2-amino-3-cyclohexylpropanoyl]amino-4-(benzyloxy)-2-hydroxybutanamide (1309974-55-7)

Guidance literature:

3-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-1-[(1,1,3,3-tetramethylbutyl)amino]carbonylpropyl (2S)-2-[(tert-butoxycarbonyl)cyclohexyl]propanoate; With trifluoroacetic acid; In dichloromethane; for 0.5h;

With triethylamine; In dichloromethane;

Reference yield:

benzyl bromide (100-39-0) → N1-(1,1,3,3-tetramethylbutyl)-(3S)-3-[(2S)-2-amino-3-cyclohexylpropanoyl]amino-4-(benzyloxy)-2-hydroxybutanamide (1309974-55-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere

1.2: 25 °C / Inert atmosphere

2.1: 4-methyl-morpholine; isobutyl chloroformate / 1,2-dimethoxyethane / -20 °C

2.2: 0.5 h / Cooling with ice

3.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C

4.1: dichloromethane / 48 h / 20 °C

5.1: trifluoroacetic acid / dichloromethane / 0.5 h

With 4-methyl-morpholine; sodium hydride; Dess-Martin periodane; trifluoroacetic acid; isobutyl chloroformate; In 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; 4.1: Passerini Reaction;

Reference yield:

N-(tert-butyloxycarbonyl)-O-benzyl-L-serinol (79069-15-1) → N1-(1,1,3,3-tetramethylbutyl)-(3S)-3-[(2S)-2-amino-3-cyclohexylpropanoyl]amino-4-(benzyloxy)-2-hydroxybutanamide (1309974-55-7)

Guidance literature:

Multi-step reaction with 3 steps

1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C

2: dichloromethane / 48 h / 20 °C

3: trifluoroacetic acid / dichloromethane / 0.5 h

With Dess-Martin periodane; trifluoroacetic acid; In dichloromethane; 2: Passerini Reaction;

upstream raw materials:

benzyl bromide

N-(tert-butyloxycarbonyl)-O-benzyl-L-serinol

BOC-O-benzyl-L-serine

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

Downstream raw materials:

N₄-[(1S)-2-((1S)-1-[(benzyloxy)methyl]-2-hydroxy-3-oxo-3-[(1,1,3,3-tetramethylbutyl)amino]propylamino)-1-(cyclohexylmethyl)-2-oxoethyl]-4-morpholinecarboxamide

N₄-[(1S)-2-((1S)-1-[(benzyloxy)methyl]-2,3-dioxo-3-[(1,1,3,3-tetramethylbutyl)amino]propylamino)-1-(cyclohexylmethyl)-2-oxoethyl]-4-morpholinecarboxamide

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