methyl (αR,2S)-2,3-dihydro-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1H-imidazo(1,2-a)indole-9-propanoate

Base Information

Chemical Name:methyl (αR,2S)-2,3-dihydro-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1H-imidazo(1,2-a)indole-9-propanoate
CAS No.:316828-33-8
Molecular Formula:C₂₆H₂₄Cl₃N₃O₇
Molecular Weight:596.851
Hs Code.:

methyl (αR,2S)-2,3-dihydro-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1H-imidazo(1,2-a)indole-9-propanoate

Synonyms:methyl (αR,2S)-2,3-dihydro-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1H-imidazo(1,2-a)indole-9-propanoate

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Chemical Property of methyl (αR,2S)-2,3-dihydro-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1H-imidazo(1,2-a)indole-9-propanoate

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Technology Process of methyl (αR,2S)-2,3-dihydro-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1H-imidazo(1,2-a)indole-9-propanoate

There total 8 articles about methyl (αR,2S)-2,3-dihydro-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1H-imidazo(1,2-a)indole-9-propanoate 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: 64.0%

: 316828-35-0
N_in-L-benzyloxycarbonylalanyl-N_a-2,2,2-trichloroethoxycarbonyl-2-iodo-D-tryptophan methyl ester

: 316828-33-8
methyl (αR,2S)-2,3-dihydro-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1H-imidazo(1,2-a)indole-9-propanoate

Guidance literature:: With potassium carbonate; tris-(o-tolyl)phosphine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In toluene; at 105 ℃; for 2h;
DOI:10.1021/ol0067686

Reference yield: 64.0%

: 316828-35-0
N_in-L-benzyloxycarbonylalanyl-N_a-2,2,2-trichloroethoxycarbonyl-2-iodo-D-tryptophan methyl ester

: 316828-31-6
N_in-L-benzyloxycarbonylalanyl-N_a-2,2,2-trichloroethoxycarbonyl-D-tryptophan methyl ester

: 316828-33-8
methyl (αR,2S)-2,3-dihydro-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1H-imidazo(1,2-a)indole-9-propanoate

Guidance literature:: With potassium carbonate; tris-(o-tolyl)phosphine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In toluene; at 105 ℃; for 2h;
DOI:10.1021/jo0264980

Reference yield:

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

: 316828-33-8
methyl (αR,2S)-2,3-dihydro-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1H-imidazo(1,2-a)indole-9-propanoate

Guidance literature:: Multi-step reaction with 5 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

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