(S)-9-((R)-2-Amino-2-methoxycarbonyl-ethyl)-2-methyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(S)-9-((R)-2-Amino-2-methoxycarbonyl-ethyl)-2-methyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester
CAS No.:496961-90-1
Molecular Formula:C₂₃H₂₃N₃O₅
Molecular Weight:421.453
Hs Code.:

Synonyms:(S)-9-((R)-2-Amino-2-methoxycarbonyl-ethyl)-2-methyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

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Chemical Property of (S)-9-((R)-2-Amino-2-methoxycarbonyl-ethyl)-2-methyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

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Technology Process of (S)-9-((R)-2-Amino-2-methoxycarbonyl-ethyl)-2-methyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

There total 8 articles about (S)-9-((R)-2-Amino-2-methoxycarbonyl-ethyl)-2-methyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl 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:

: 14907-27-8,5619-09-0,7524-52-9,26988-71-6,41222-70-2,67557-19-1,109492-62-8
(R)-(+)-tryptophan methyl ester hydrochloride

: 496961-90-1
(S)-9-((R)-2-Amino-2-methoxycarbonyl-ethyl)-2-methyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 96 percent / NaHCO₃ / diethyl ether; H₂O / 4 h / 20 °C

2.1: 92 percent / BH₃*THF / tetrahydrofuran; trifluoroacetic acid / 1 h / 0 °C

3.1: DCC / CH₂Cl₂ / 0.33 h / 20 °C

4.1: 3.53 g / DDQ / toluene / 2 h / 110 °C

5.1: Hg(OTFA)2 / CH₂Cl₂ / 0.33 h / 20 °C

5.2: 85 percent / I₂ / CH₂Cl₂ / 3 h / 20 °C

6.1: 64 percent / P(o-tolyl)3; K₂CO₃ / Pd₂(dba)3 / toluene / 2 h / 105 °C

7.1: Zn; AcOH / 0.5 h / 20 °C

With borane-THF; mercury(II) trifluoroacetate; sodium hydrogencarbonate; potassium carbonate; acetic acid; dicyclohexyl-carbodiimide; tris-(o-tolyl)phosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; trifluoroacetic acid;
DOI:10.1021/jo0264980

Reference yield:

: 316828-30-5
N_α-2,2,2-trichloroethoxycarbonyl-D-tryptophan methyl ester

: 496961-90-1
(S)-9-((R)-2-Amino-2-methoxycarbonyl-ethyl)-2-methyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 92 percent / BH₃*THF / tetrahydrofuran; trifluoroacetic acid / 1 h / 0 °C

2.1: DCC / CH₂Cl₂ / 0.33 h / 20 °C

3.1: 3.53 g / DDQ / toluene / 2 h / 110 °C

4.1: Hg(OTFA)2 / CH₂Cl₂ / 0.33 h / 20 °C

4.2: 85 percent / I₂ / CH₂Cl₂ / 3 h / 20 °C

5.1: 64 percent / P(o-tolyl)3; K₂CO₃ / Pd₂(dba)3 / toluene / 2 h / 105 °C

6.1: Zn; AcOH / 0.5 h / 20 °C

With borane-THF; mercury(II) trifluoroacetate; potassium carbonate; acetic acid; dicyclohexyl-carbodiimide; tris-(o-tolyl)phosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; dichloromethane; toluene; trifluoroacetic acid;
DOI:10.1021/jo0264980

Reference yield:

: 1142-20-7
N-Cbz-Ala

: 496961-90-1
(S)-9-((R)-2-Amino-2-methoxycarbonyl-ethyl)-2-methyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: DCC / CH₂Cl₂ / 0.33 h / 20 °C

2.1: 3.53 g / DDQ / toluene / 2 h / 110 °C

3.1: Hg(OTFA)2 / CH₂Cl₂ / 0.33 h / 20 °C

3.2: 85 percent / I₂ / CH₂Cl₂ / 3 h / 20 °C

4.1: 64 percent / P(o-tolyl)3; K₂CO₃ / Pd₂(dba)3 / toluene / 2 h / 105 °C

5.1: Zn; AcOH / 0.5 h / 20 °C

With mercury(II) trifluoroacetate; potassium carbonate; acetic acid; dicyclohexyl-carbodiimide; tris-(o-tolyl)phosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In dichloromethane; toluene;
DOI:10.1021/jo0264980