N-<1-phenyl-2(S)-amino>-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide

Base Information

• Chemical Name: N-<1-phenyl-2(S)-amino>-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide
• CAS No.: 142580-72-1
• Molecular Formula: C₃₇H₄₇N₅O₇
• Molecular Weight: 673.809

Synonyms:N-<1-phenyl-2(S)-amino>-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide

Chemical Property of N-<1-phenyl-2(S)-amino>-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide

Chemical Property:

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Technology Process of N-<1-phenyl-2(S)-amino>-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide

There total 6 articles about N-<1-phenyl-2(S)-amino>-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide 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: 84.0%

N-tert-butyloxycarbonylasparagine (7536-55-2) + N-<1-phenyl-2(S)-amino-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide (142580-71-0) → N-<1-phenyl-2(S)-amino>-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide (142580-72-1)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; In dichloromethane; ethyl acetate; for 18h; Ambient temperature;

DOI:10.1021/jm00092a002

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → N-<1-phenyl-2(S)-amino>-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide (142580-72-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 5.50 g / 1-ethyl-3-<(3-dimethylamino)propyl>carbodiimide*HCl, 1-hydroxybenzotriazole hydrate, triethylamine / dimethylformamide / 18 h / Ambient temperature

2: 89 percent / trifluoroacetic acid / CHCl₃ / 3 h / Ambient temperature

3: 35 percent / W-200-N alumina / tetrahydrofuran; diethyl ether / 72 h / Ambient temperature

4: 72 percent / 2 N aq. HCl / methanol / 2 h / 60 °C

5: 84 percent / 3-hydroxy-1,2,3-benzotriazin-4(3H)-one (HOOBT), 1-ethyl-3-<(3-dimethylamino)propyl>carbodiimide*HCl, diisopropylethylamine / ethyl acetate; CH₂Cl₂ / 18 h / Ambient temperature

With hydrogenchloride; W-200-N alumina; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00092a002

Reference yield:

(1S,2R)-1-amino-2-indanol (7480-35-5,13286-59-4,74165-73-4,126456-43-7,136030-00-7,140632-19-5,140632-20-8) → N-<1-phenyl-2(S)-amino>-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide (142580-72-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 5.50 g / 1-ethyl-3-<(3-dimethylamino)propyl>carbodiimide*HCl, 1-hydroxybenzotriazole hydrate, triethylamine / dimethylformamide / 18 h / Ambient temperature

2: 89 percent / trifluoroacetic acid / CHCl₃ / 3 h / Ambient temperature

3: 35 percent / W-200-N alumina / tetrahydrofuran; diethyl ether / 72 h / Ambient temperature

4: 72 percent / 2 N aq. HCl / methanol / 2 h / 60 °C

5: 84 percent / 3-hydroxy-1,2,3-benzotriazin-4(3H)-one (HOOBT), 1-ethyl-3-<(3-dimethylamino)propyl>carbodiimide*HCl, diisopropylethylamine / ethyl acetate; CH₂Cl₂ / 18 h / Ambient temperature

With hydrogenchloride; W-200-N alumina; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00092a002

upstream raw materials:

N-tert-butyloxycarbonylasparagine

N-<1-phenyl-2(S)-amino-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide

N-tert-butoxycarbonyl-L-phenylalanine

(1S,2R)-1-amino-2-indanol

Downstream raw materials:

N-<1-phenyl-2(S)-<amino>-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide

N-<1-phenyl-2(S)-(N-L-asparaginylamino)-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide

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