2-<(methoxycarbonyl)methyl>-3-<2-(S)-(benzyloxycarbonyl)-2-(N^b-benzyl)aminoethyl>indole

Base Information

• Chemical Name: 2-<(methoxycarbonyl)methyl>-3-<2-(S)-(benzyloxycarbonyl)-2-(N^b-benzyl)aminoethyl>indole
• CAS No.: 198954-39-1
• Molecular Formula: C₂₈H₂₈N₂O₄
• Molecular Weight: 456.541

Synonyms:2-<(methoxycarbonyl)methyl>-3-<2-(S)-(benzyloxycarbonyl)-2-(N^b-benzyl)aminoethyl>indole

Chemical Property of 2-<(methoxycarbonyl)methyl>-3-<2-(S)-(benzyloxycarbonyl)-2-(N^b-benzyl)aminoethyl>indole

Chemical Property:

Purity/Quality:

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Technology Process of 2-<(methoxycarbonyl)methyl>-3-<2-(S)-(benzyloxycarbonyl)-2-(N^b-benzyl)aminoethyl>indole

There total 7 articles about 2-<(methoxycarbonyl)methyl>-3-<2-(S)-(benzyloxycarbonyl)-2-(N^b-benzyl)aminoethyl>indole 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: 91.0%

(S)-2-(Benzyl-tert-butoxycarbonyl-amino)-3-(2-methoxycarbonylmethyl-1H-indol-3-yl)-propionic acid benzyl ester (198954-46-0) → 2-<(methoxycarbonyl)methyl>-3-<2-(S)-(benzyloxycarbonyl)-2-(Nb-benzyl)aminoethyl>indole (198954-39-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1021/jo970207j

Reference yield:

L-tryptophane benzyl ester (4299-69-8,141595-98-4) → 2-<(methoxycarbonyl)methyl>-3-<2-(S)-(benzyloxycarbonyl)-2-(Nb-benzyl)aminoethyl>indole (198954-39-1)

Guidance literature:

Multi-step reaction with 6 steps

1: MgSO₄ / CH₂Cl₂ / 8 h

2: 95 percent / NaBH₄ / methanol / 1 h / 0 °C

3: 96 percent / K₂CO₃ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

4: Et₃N, t-BuOCl, ZnCl₂ / tetrahydrofuran; diethyl ether / 1.) -78 deg C, 1 h, 2.) room temperature, 1 h

5: 87 percent / LiCl / dimethylformamide / 3 h / 130 °C

6: 91 percent / Et₃N, TMSOTf / CH₂Cl₂ / 2 h / Ambient temperature

With sodium tetrahydroborate; tert-butylhypochlorite; trimethylsilyl trifluoromethanesulfonate; magnesium sulfate; potassium carbonate; triethylamine; lithium chloride; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo970207j

Reference yield:

benzaldehyde (100-52-7) → 2-<(methoxycarbonyl)methyl>-3-<2-(S)-(benzyloxycarbonyl)-2-(Nb-benzyl)aminoethyl>indole (198954-39-1)

Guidance literature:

Multi-step reaction with 6 steps

1: MgSO₄ / CH₂Cl₂ / 8 h

2: 95 percent / NaBH₄ / methanol / 1 h / 0 °C

3: 96 percent / K₂CO₃ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

4: Et₃N, t-BuOCl, ZnCl₂ / tetrahydrofuran; diethyl ether / 1.) -78 deg C, 1 h, 2.) room temperature, 1 h

5: 87 percent / LiCl / dimethylformamide / 3 h / 130 °C

6: 91 percent / Et₃N, TMSOTf / CH₂Cl₂ / 2 h / Ambient temperature

With sodium tetrahydroborate; tert-butylhypochlorite; trimethylsilyl trifluoromethanesulfonate; magnesium sulfate; potassium carbonate; triethylamine; lithium chloride; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo970207j

upstream raw materials:

(S)-2-(Benzyl-tert-butoxycarbonyl-amino)-3-(2-methoxycarbonylmethyl-1H-indol-3-yl)-propionic acid benzyl ester

L-tryptophane benzyl ester

benzaldehyde

(S)-2-Benzylamino-3-(1H-indol-3-yl)-propionic acid benzyl ester

Downstream raw materials:

(2S,3aS,5R,11bR)-3-Benzyl-5-methyl-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester

methyl (2S,3aS,5R,11bR)-2-(benzyloxycarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

(2S,3aS,5R,11bR)-3-Benzyl-2-cyano-5-methyl-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylic acid methyl ester

(2S,3aS,5R,11bR)-3-Benzyl-2-carbamoyl-5-methyl-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylic acid methyl ester

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