(2S)-2-methyl-N-[N-phthaloyl-(2S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline

Base Information

• Chemical Name: (2S)-2-methyl-N-[N-phthaloyl-(2S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline
• CAS No.: 1239896-96-8
• Molecular Formula: C₂₇H₂₄N₂O₃
• Molecular Weight: 424.499

Synonyms:(2S)-2-methyl-N-[N-phthaloyl-(2S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline

Chemical Property of (2S)-2-methyl-N-[N-phthaloyl-(2S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline

Chemical Property:

Purity/Quality:

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Technology Process of (2S)-2-methyl-N-[N-phthaloyl-(2S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline

There total 7 articles about (2S)-2-methyl-N-[N-phthaloyl-(2S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline 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:

1,2,3,4-tetrahydro-2-methylquinoline (1780-19-4) + phthaloyl-L-phenylalanyl chloride (32150-91-7) → (2R)-2-methyl-N-[N-phthaloyl-(2S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline (1239897-00-7) + (2S)-2-methyl-N-[N-phthaloyl-(2S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline (1239896-96-8) + (S)-2-methyl-1,2,3,4-tetrahydroquinoline (200125-70-8) + (R)-1,2,3,4-tetrahydroquinaldine (1780-19-4,63430-95-5,74497-74-8)

Guidance literature:

In dichloromethane; at -20 ℃; for 6h; optical yield given as %ee; stereoselective reaction;

DOI:10.1016/j.tetasy.2010.12.017

Reference yield:

2-methylquinoline (91-63-4) → (2R)-2-methyl-N-[N-phthaloyl-(2S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline (1239897-00-7) + (2S)-2-methyl-N-[N-phthaloyl-(2S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline (1239896-96-8) + (R)-1,2,3,4-tetrahydroquinaldine (1780-19-4,63430-95-5,74497-74-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium; ethanol / 20 - 50 °C

2: dichloromethane / 6 h / -20 °C / Resolution of racemate

With ethanol; sodium; In dichloromethane;

DOI:10.1016/j.tetasy.2013.07.024

Reference yield:

1,2,3,4-tetrahydro-2-methylquinoline (1780-19-4) + phthaloyl-L-phenylalanyl chloride (32150-91-7) → (2S)-2-methyl-N-[N-phthaloyl-(2S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline (1239896-96-8) + (S)-2-methyl-1,2,3,4-tetrahydroquinoline (200125-70-8) + (R)-1,2,3,4-tetrahydroquinaldine (1780-19-4,63430-95-5,74497-74-8) + N-[N'-phthaloyl-(2S)-alanyl]-(2R)-2-methyl-1,2,3,4-tetrahydroquinoline

Guidance literature:

In dichloromethane; at 20 ℃; for 6h; optical yield given as %ee; stereoselective reaction;

DOI:10.1016/j.tetasy.2010.05.013

upstream raw materials:

1,2,3,4-tetrahydro-2-methylquinoline

phthaloyl-L-phenylalanyl chloride

L-phenylalanine

Nα-phthaloyl-L-phenylalanine

Downstream raw materials:

(S)-2-methyl-1,2,3,4-tetrahydroquinoline

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