(S)-2-{[3-(N-phthalimido)adamantan-1-yl]carboxamido}-3-phenylpropanoic acid

Base Information

• Chemical Name: (S)-2-{[3-(N-phthalimido)adamantan-1-yl]carboxamido}-3-phenylpropanoic acid
• CAS No.: 1617511-45-1
• Molecular Formula: C₂₈H₂₈N₂O₅
• Molecular Weight: 472.541
• Mol file: 1617511-45-1.mol

Synonyms:(S)-2-{[3-(N-phthalimido)adamantan-1-yl]carboxamido}-3-phenylpropanoic acid

Chemical Property of (S)-2-{[3-(N-phthalimido)adamantan-1-yl]carboxamido}-3-phenylpropanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of (S)-2-{[3-(N-phthalimido)adamantan-1-yl]carboxamido}-3-phenylpropanoic acid

There total 2 articles about (S)-2-{[3-(N-phthalimido)adamantan-1-yl]carboxamido}-3-phenylpropanoic acid 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:

3-(N-phthalimido)-1-adamantane carboxylic acid (1333108-05-6) → (S)-2-{[3-(N-phthalimido)adamantan-1-yl]carboxamido}-3-phenylpropanoic acid (1617511-45-1)

Guidance literature:

Multi-step reaction with 2 steps

1: dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

2: triethylamine; water / tetrahydrofuran / 72 h / 20 °C

With water; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2014.05.118

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + 3-(N-phthalimido)-1-adamantane carboxylic acid (1333108-05-6) → (S)-2-{[3-(N-phthalimido)adamantan-1-yl]carboxamido}-3-phenylpropanoic acid (1617511-45-1)

Guidance literature:

3-(N-phthalimido)-1-adamantane carboxylic acid; With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide;

L-phenylalanine; Alkaline conditions;

DOI:10.5562/cca2482

Reference yield: 65.0%

methanol (67-56-1) + (S)-2-{[3-(N-phthalimido)adamantan-1-yl]carboxamido}-3-phenylpropanoic acid (1617511-45-1) → (11R)-2,12-diaza-11-benzylpentacyclo[12.5.1.11,16.114,18.04,9]doeicosa-4,6,8-trien-3,10,13-trione + 2,12-diaza-10-methoxy-11-benzylpentacyclo[12.5.1.11,16.114,18.04,9]doeicosa-4,6,8-trien-3,13-dione + N-[3-(2-phenylethan-1-yl)carbamoyladamantan-1-yl]phthalimide (1617511-46-2)

Guidance literature:

(S)-2-{[3-(N-phthalimido)adamantan-1-yl]carboxamido}-3-phenylpropanoic acid; With potassium carbonate; In water; acetone; Inert atmosphere; UV-irradiation;

methanol; In dichloromethane; enantioselective reaction;

DOI:10.1016/j.tetlet.2014.05.118

upstream raw materials:

3-(N-phthalimido)-1-adamantane carboxylic acid

L-phenylalanine

Downstream raw materials:

N-[3-(2-phenylethan-1-yl)carbamoyladamantan-1-yl]phthalimide