N₁-((S)-1-(4-(hex-5-enyloxy)phenyl)-2-hydroxyethyl)-N₃-((R)-1-hydroxy-3-(4-(undec-10-enyloxy)phenyl)propan-2-yl)-2,2-dimethylmalonamide

Base Information

• Chemical Name: N₁-((S)-1-(4-(hex-5-enyloxy)phenyl)-2-hydroxyethyl)-N₃-((R)-1-hydroxy-3-(4-(undec-10-enyloxy)phenyl)propan-2-yl)-2,2-dimethylmalonamide
• CAS No.: 1415547-06-6
• Molecular Formula: C₃₉H₅₈N₂O₆
• Molecular Weight: 650.899

Synonyms:N₁-((S)-1-(4-(hex-5-enyloxy)phenyl)-2-hydroxyethyl)-N₃-((R)-1-hydroxy-3-(4-(undec-10-enyloxy)phenyl)propan-2-yl)-2,2-dimethylmalonamide

Chemical Property of N₁-((S)-1-(4-(hex-5-enyloxy)phenyl)-2-hydroxyethyl)-N₃-((R)-1-hydroxy-3-(4-(undec-10-enyloxy)phenyl)propan-2-yl)-2,2-dimethylmalonamide

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Technology Process of N₁-((S)-1-(4-(hex-5-enyloxy)phenyl)-2-hydroxyethyl)-N₃-((R)-1-hydroxy-3-(4-(undec-10-enyloxy)phenyl)propan-2-yl)-2,2-dimethylmalonamide

There total 6 articles about N₁-((S)-1-(4-(hex-5-enyloxy)phenyl)-2-hydroxyethyl)-N₃-((R)-1-hydroxy-3-(4-(undec-10-enyloxy)phenyl)propan-2-yl)-2,2-dimethylmalonamide 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: 73.0%

(R)-2-amino-3-(4-(undec-10-enyloxy)phenyl)propan-1-ol (1415547-08-8) + (S)-3-(1-(4-(hex-5-enyloxy)phenyl)-2-hydroxyethylamino)-2,2-dimethyl-3-oxopropanoic acid (1415547-15-7) → N1-((S)-1-(4-(hex-5-enyloxy)phenyl)-2-hydroxyethyl)-N3-((R)-1-hydroxy-3-(4-(undec-10-enyloxy)phenyl)propan-2-yl)-2,2-dimethylmalonamide (1415547-06-6)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 93h; Inert atmosphere;

DOI:10.1016/j.tet.2012.10.069

Reference yield:

3-ethoxy-2,2-dimethyl-3-oxopropanoic acid (5471-77-2) → N1-((S)-1-(4-(hex-5-enyloxy)phenyl)-2-hydroxyethyl)-N3-((R)-1-hydroxy-3-(4-(undec-10-enyloxy)phenyl)propan-2-yl)-2,2-dimethylmalonamide (1415547-06-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / chloroform / 1.5 h / 0 °C / Inert atmosphere

1.2: 18 h / 20 °C / Inert atmosphere

2.1: sodium hydroxide / tetrahydrofuran; water / 4 h / 45 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dichloromethane; N,N-dimethyl-formamide / 93 h / 20 °C / Inert atmosphere

With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; dichloromethane; chloroform; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2012.10.069

Reference yield:

(S)-ethyl 3-(1-(4-(hex-5-enyloxy)phenyl)-2-hydroxyethylamino)-2,2-dimethyl-3-oxopropanoate (1415547-29-3) → N1-((S)-1-(4-(hex-5-enyloxy)phenyl)-2-hydroxyethyl)-N3-((R)-1-hydroxy-3-(4-(undec-10-enyloxy)phenyl)propan-2-yl)-2,2-dimethylmalonamide (1415547-06-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / tetrahydrofuran; water / 4 h / 45 °C / Inert atmosphere

2: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dichloromethane; N,N-dimethyl-formamide / 93 h / 20 °C / Inert atmosphere

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2012.10.069

upstream raw materials:

(S)-hydroxyphenylglycine

(S)-methyl 2-(4-hydroxyphenyl)-2-(methoxycarbonylamino)acetate

(R)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(undec-10-enyloxy)phenyl)propanoate

(R)-2-amino-3-(4-(undec-10-enyloxy)phenyl)propan-1-ol

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