[(1S,2R,3S,4S)-3-((S)-1-Methylcarbamoyl-2-phenyl-ethylcarbamoyl)-1,2,3,4-tetrahydro-1,4-methano-naphthalen-2-yl]-carbamic acid methyl ester

Base Information

Chemical Name:[(1S,2R,3S,4S)-3-((S)-1-Methylcarbamoyl-2-phenyl-ethylcarbamoyl)-1,2,3,4-tetrahydro-1,4-methano-naphthalen-2-yl]-carbamic acid methyl ester
CAS No.:854278-96-9
Molecular Formula:C₂₄H₂₇N₃O₄
Molecular Weight:421.496
Hs Code.:

Synonyms:[(1S,2R,3S,4S)-3-((S)-1-Methylcarbamoyl-2-phenyl-ethylcarbamoyl)-1,2,3,4-tetrahydro-1,4-methano-naphthalen-2-yl]-carbamic acid methyl ester

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Chemical Property of [(1S,2R,3S,4S)-3-((S)-1-Methylcarbamoyl-2-phenyl-ethylcarbamoyl)-1,2,3,4-tetrahydro-1,4-methano-naphthalen-2-yl]-carbamic acid methyl ester

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Technology Process of [(1S,2R,3S,4S)-3-((S)-1-Methylcarbamoyl-2-phenyl-ethylcarbamoyl)-1,2,3,4-tetrahydro-1,4-methano-naphthalen-2-yl]-carbamic acid methyl ester

There total 7 articles about [(1S,2R,3S,4S)-3-((S)-1-Methylcarbamoyl-2-phenyl-ethylcarbamoyl)-1,2,3,4-tetrahydro-1,4-methano-naphthalen-2-yl]-carbamic acid methyl ester 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: 29.0%

: (1R,2R,3S,4R)-3-Methoxycarbonylamino-1,2,3,4-tetrahydro-1,4-methano-naphthalene-2-carboxylic acid

: 17186-56-0,111321-55-2
L-phenylalanine methylamide hydrochloride

: 854278-96-9
[(1S,2R,3S,4S)-3-((S)-1-Methylcarbamoyl-2-phenyl-ethylcarbamoyl)-1,2,3,4-tetrahydro-1,4-methano-naphthalen-2-yl]-carbamic acid methyl ester

: 854278-95-8
[(1R,2S,3R,4R)-3-((S)-1-Methylcarbamoyl-2-phenyl-ethylcarbamoyl)-1,2,3,4-tetrahydro-1,4-methano-naphthalen-2-yl]-carbamic acid methyl ester

Guidance literature:: (1R,2R,3S,4R)-3-Methoxycarbonylamino-1,2,3,4-tetrahydro-1,4-methano-naphthalene-2-carboxylic acid; With 1,1'-carbonyldiimidazole; In dichloromethane; at 20 ℃; for 1h;

L-phenylalanine methylamide hydrochloride; In dichloromethane; at 20 ℃;
DOI:10.1021/jo0479563

Reference yield:

: (1R,2R,3S,4S)-1,2,3,4-Tetrahydro-1,4-methano-naphthalene-2,3-dicarboxylic acid monomethyl ester

: 854278-96-9
[(1S,2R,3S,4S)-3-((S)-1-Methylcarbamoyl-2-phenyl-ethylcarbamoyl)-1,2,3,4-tetrahydro-1,4-methano-naphthalen-2-yl]-carbamic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetrahydrofuran / 0.5 h / 0 °C

2.1: 699 mg / NaN₃ / tetrahydrofuran; H₂O / 4 h / 20 °C

3.1: 74 percent / toluene / 5 h / Heating

4.1: 90 percent / LiOH*H₂O / H₂O; methanol / 3 h / 20 °C

5.1: CDI / CH₂Cl₂ / 1 h / 20 °C

5.2: 29 percent / CH₂Cl₂ / 20 °C

With lithium hydroxide; sodium azide; 1,1'-carbonyldiimidazole; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 3.1: Schmidt rearrangement;
DOI:10.1021/jo0479563

Reference yield:

: (1R,2R,3S,4R)-3-Methoxycarbonylamino-1,2,3,4-tetrahydro-1,4-methano-naphthalene-2-carboxylic acid methyl ester

: 854278-96-9
[(1S,2R,3S,4S)-3-((S)-1-Methylcarbamoyl-2-phenyl-ethylcarbamoyl)-1,2,3,4-tetrahydro-1,4-methano-naphthalen-2-yl]-carbamic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 90 percent / LiOH*H₂O / H₂O; methanol / 3 h / 20 °C

2.1: CDI / CH₂Cl₂ / 1 h / 20 °C

2.2: 29 percent / CH₂Cl₂ / 20 °C

With lithium hydroxide; 1,1'-carbonyldiimidazole; In methanol; dichloromethane; water;
DOI:10.1021/jo0479563