methyl (1S,3S,1'R)-1-[1'-(9-fluorenylmethoxycarbonyl)amino-2'-phenylethyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate

Base Information

• Chemical Name: methyl (1S,3S,1'R)-1-[1'-(9-fluorenylmethoxycarbonyl)amino-2'-phenylethyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate
• CAS No.: 1034299-71-2
• Molecular Formula: C₃₆H₃₃N₃O₄
• Molecular Weight: 571.676

Synonyms:methyl (1S,3S,1'R)-1-[1'-(9-fluorenylmethoxycarbonyl)amino-2'-phenylethyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate

Chemical Property of methyl (1S,3S,1'R)-1-[1'-(9-fluorenylmethoxycarbonyl)amino-2'-phenylethyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate

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Technology Process of methyl (1S,3S,1'R)-1-[1'-(9-fluorenylmethoxycarbonyl)amino-2'-phenylethyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate

There total 1 articles about methyl (1S,3S,1'R)-1-[1'-(9-fluorenylmethoxycarbonyl)amino-2'-phenylethyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate 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: 16.0%

(S)-tryptophan methyl ester hydrochloride (7524-52-9,26988-71-6,5619-09-0,14907-27-8,41222-70-2,67557-19-1,109492-62-8) + (-)-(R)-(N-9-fluorenylmethoxycarbonyl)phenylalaninal (146803-47-6) → 5-(9-fluorenylmethyl) 2-methyl (2S,3aS,4R,5aR,10bS)-4-benzyl-1,2,3,3a,4,5,5a,6-octahydropyrrolo[3',2':3,4]pyrrolo[2,3-b]indole-2,5-dicarboxylate (1034299-75-6) + methyl (1R,3S,1'R)-1-[1'-(9-fluorenylmethoxycarbonyl)amino-2'-phenylethyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate (1034299-73-4) + methyl (1S,3S,1'R)-1-[1'-(9-fluorenylmethoxycarbonyl)amino-2'-phenylethyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate (1034299-71-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1002/ejoc.200701172

Reference yield: 87.0%

methyl (1S,3S,1'R)-1-[1'-(9-fluorenylmethoxycarbonyl)amino-2'-phenylethyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate (1034299-71-2) → (6S,7R,10S)-7-benzyl-6,10-imino-6,7,8,9,10,11-hexahydro-5H-azocino[4,5-b]indol-9-one (1072107-39-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1002/ejoc.200701172

Reference yield:

methyl (1S,3S,1'R)-1-[1'-(9-fluorenylmethoxycarbonyl)amino-2'-phenylethyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylate (1034299-71-2) + di-tert-butyl dicarbonate (24424-99-5) → C41H41N3O6

Guidance literature:

With potassium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 16h;

DOI:10.1002/ejoc.200701172

upstream raw materials:

(S)-tryptophan methyl ester hydrochloride

(-)-(R)-(N-9-fluorenylmethoxycarbonyl)phenylalaninal

Downstream raw materials:

(6S,7R,10S)-7-benzyl-6,10-imino-6,7,8,9,10,11-hexahydro-5H-azocino[4,5-b]indol-9-one

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