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

Base Information

• Chemical Name: N-<1-phenyl-2(S)-<(tert-butoxycarbonyl)amino>-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide
• CAS No.: 142694-73-3
• Molecular Formula: C₃₃H₄₁N₃O₅
• Molecular Weight: 559.706
• Mol file: 142694-73-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about N-<1-phenyl-2(S)-<(tert-butoxycarbonyl)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: 35.0%

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester (98760-08-8,98818-34-9,98818-35-0,103127-56-6,98737-29-2) + (L)-phenylalanine <2(R)-hydroxy-1(S)-indanyl>amide (140468-56-0) → N-<1-phenyl-2(S)-<(tert-butoxycarbonyl)amino>-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide (142694-73-3)

Guidance literature:

With W-200-N alumina; In tetrahydrofuran; diethyl ether; for 72h; Ambient temperature;

DOI:10.1021/jm00092a002

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → N-<1-phenyl-2(S)-<(tert-butoxycarbonyl)amino>-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide (142694-73-3)

Guidance literature:

Multi-step reaction with 3 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

With W-200-N alumina; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; chloroform; 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)-<(tert-butoxycarbonyl)amino>-3(R)-hydroxybutan-4-yl>-L-phenylalanine (2(R)-hydroxy-1(S)-indanyl)amide (142694-73-3)

Guidance literature:

Multi-step reaction with 3 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

With W-200-N alumina; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jm00092a002

upstream raw materials:

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester

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

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

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