N¹-((2S,3R)-3-hydroxy-4-nitro-1-phenylbutan-2-yl)-N³,N³-dipropylisophthalamide

Base Information

• Chemical Name: N¹-((2S,3R)-3-hydroxy-4-nitro-1-phenylbutan-2-yl)-N³,N³-dipropylisophthalamide
• CAS No.: 1422208-32-9
• Molecular Formula: C₂₄H₃₁N₃O₅
• Molecular Weight: 441.527

Synonyms:N¹-((2S,3R)-3-hydroxy-4-nitro-1-phenylbutan-2-yl)-N³,N³-dipropylisophthalamide

Chemical Property of N¹-((2S,3R)-3-hydroxy-4-nitro-1-phenylbutan-2-yl)-N³,N³-dipropylisophthalamide

Chemical Property:

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Technology Process of N¹-((2S,3R)-3-hydroxy-4-nitro-1-phenylbutan-2-yl)-N³,N³-dipropylisophthalamide

There total 2 articles about N¹-((2S,3R)-3-hydroxy-4-nitro-1-phenylbutan-2-yl)-N³,N³-dipropylisophthalamide 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: 86.0%

(2R,3S)-3-amino-1-nitro-4-phenylbutan-2-ol hydrochloride (1422207-48-4) + N,N-Dipropylisophthalamic acid (126926-35-0) → N1-((2S,3R)-3-hydroxy-4-nitro-1-phenylbutan-2-yl)-N3,N3-dipropylisophthalamide (1422208-32-9)

Guidance literature:

With N-ethylmorpholine;; HATU; In dimethyl sulfoxide; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.bmcl.2012.11.118

Reference yield:

(2S,3R)-N-tert-butyloxycarbonyl-2-amino-3-hydroxy-1-phenyl-4-nitrobutane (161282-72-0) → N1-((2S,3R)-3-hydroxy-4-nitro-1-phenylbutan-2-yl)-N3,N3-dipropylisophthalamide (1422208-32-9)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / 1,4-dioxane; dichloromethane / 20 h / 20 °C / Inert atmosphere

2: N-ethylmorpholine;; HATU / dimethyl sulfoxide / 16 h / 20 °C / Inert atmosphere

With N-ethylmorpholine;; hydrogenchloride; HATU; In 1,4-dioxane; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/j.bmcl.2012.11.118

Reference yield: 64.0%

N1-((2S,3R)-3-hydroxy-4-nitro-1-phenylbutan-2-yl)-N3,N3-dipropylisophthalamide (1422208-32-9) → N1-((2S,3R)-4-amino-3-hydroxy-1-phenylbutan-2-yl)-N3,N3-dipropylisophthalamide (660431-13-0)

Guidance literature:

With palladium 10% on activated carbon; ammonium formate; In methanol; at 50 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.bmcl.2012.11.118

upstream raw materials:

(2R,3S)-3-amino-1-nitro-4-phenylbutan-2-ol hydrochloride

N,N-Dipropylisophthalamic acid

(2S,3R)-N-tert-butyloxycarbonyl-2-amino-3-hydroxy-1-phenyl-4-nitrobutane

Downstream raw materials:

N₁-[(1S,2R)-1-benzyl-2-hydroxy-3-(isopropylamino)propyl]-N₃,N₃-dipropylisophthalamide

C₂₉H₄₁N₃O₄

C₂₉H₄₁N₃O₃

C₃₀H₄₄N₄O₃

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