N-(L-phenylalanyl)-1(R)-amino-2(S)-hydroxyindan

Base Information

• Chemical Name: N-(L-phenylalanyl)-1(R)-amino-2(S)-hydroxyindan
• CAS No.: 140468-57-1
• Molecular Formula: C₁₈H₂₀N₂O₂
• Molecular Weight: 296.369
• Mol file: 140468-57-1.mol

Synonyms:N-(L-phenylalanyl)-1(R)-amino-2(S)-hydroxyindan

Chemical Property of N-(L-phenylalanyl)-1(R)-amino-2(S)-hydroxyindan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(L-phenylalanyl)-1(R)-amino-2(S)-hydroxyindan

There total 5 articles about N-(L-phenylalanyl)-1(R)-amino-2(S)-hydroxyindan 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: 40.0%

[(R)-1-((1S,2R)-2-Hydroxy-indan-1-ylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester (140468-58-2,140468-59-3) → (L)-phenylalanine <2(R)-hydroxy-1(S)-indanyl>amide (140468-56-0) + N-(L-phenylalanyl)-1(R)-amino-2(S)-hydroxyindan (140468-57-1)

Guidance literature:

With trifluoroacetic acid; In chloroform; for 2.5h;

DOI:10.1021/jm00088a003

Reference yield:

(+/-)-cis-1-amino-indan-2-ol (7480-35-5,13286-59-4,74165-73-4,126456-43-7,136030-00-7,140632-19-5,140632-20-8) → N-(L-phenylalanyl)-1(R)-amino-2(S)-hydroxyindan (140468-57-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / 1-hydroxybenzotriazole hydrate, dimethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, triethylamine / dimethylformamide / 16 h

2: 40 percent / trifluoroacetic acid / CHCl₃ / 2.5 h

With dimethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride; 1-hydroxybenzotriazol-hydrate; triethylamine; trifluoroacetic acid; In chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jm00088a003

Reference yield:

trans-1-aminoindan-2-ol (7480-35-5,13286-59-4,74165-73-4,126456-43-7,136030-00-7,140632-19-5,140632-20-8) → N-(L-phenylalanyl)-1(R)-amino-2(S)-hydroxyindan (140468-57-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 20percent aq. NaOH / toluene / 24 h

2: SOCl₂ / CH₂Cl₂ / 16 h / Ambient temperature

3: 88 percent / aq. H₂SO₄ / H₂O / 16 h / Heating

4: 97 percent / 1-hydroxybenzotriazole hydrate, dimethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, triethylamine / dimethylformamide / 16 h

5: 40 percent / trifluoroacetic acid / CHCl₃ / 2.5 h

With sodium hydroxide; thionyl chloride; dimethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride; sulfuric acid; 1-hydroxybenzotriazol-hydrate; triethylamine; trifluoroacetic acid; In dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00088a003

upstream raw materials:

[(R)-1-((1S,2R)-2-Hydroxy-indan-1-ylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

(+/-)-cis-1-amino-indan-2-ol

trans-1-aminoindan-2-ol

2-phenyl-3a,8a-dihydro-8(H)-indeno<1,2-d>oxazole

Refernces