methyl (αR,2S,9S)-2,3,9,9a-tetrahydro-9-hydroxy-9a-methoxy-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,9S)-2,3,9,9a-tetrahydro-9-hydroxy-9a-methoxy-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1H-imidazo(1,2-a)indole-9-propanoate
CAS No.:316828-44-1
Molecular Formula:C₂₇H₂₈Cl₃N₃O₉
Molecular Weight:644.893
Hs Code.:

methyl (αR,2S,9S)-2,3,9,9a-tetrahydro-9-hydroxy-9a-methoxy-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,9S)-2,3,9,9a-tetrahydro-9-hydroxy-9a-methoxy-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,9S)-2,3,9,9a-tetrahydro-9-hydroxy-9a-methoxy-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,9S)-2,3,9,9a-tetrahydro-9-hydroxy-9a-methoxy-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,9S)-2,3,9,9a-tetrahydro-9-hydroxy-9a-methoxy-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: 65.0%

: 67-56-1
methanol

: 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

: 316828-44-1
methyl (αR,2S,9S)-2,3,9,9a-tetrahydro-9-hydroxy-9a-methoxy-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1H-imidazo(1,2-a)indole-9-propanoate

: 316828-45-2
methyl (αR,2S,9R)-2,3,9,9a-tetrahydro-9-hydroxy-9a-methoxy-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 7b-Bu-7bH-oxaziridino[2,3-b][1,2]benzisothiazole-3,3-dioxide; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1021/jo0264980

Reference yield:

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

: 316828-44-1
methyl (αR,2S,9S)-2,3,9,9a-tetrahydro-9-hydroxy-9a-methoxy-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 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: 65 percent / 7b-Bu-7bH-oxaziridino[2,3-b][1,2]benzisothiazole-3,3-dioxide / CH₂Cl₂ / 12 h / 20 °C

With borane-THF; 7b-Bu-7bH-oxaziridino[2,3-b][1,2]benzisothiazole-3,3-dioxide; 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

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

: 316828-44-1
methyl (αR,2S,9S)-2,3,9,9a-tetrahydro-9-hydroxy-9a-methoxy-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 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: 65 percent / 7b-Bu-7bH-oxaziridino[2,3-b][1,2]benzisothiazole-3,3-dioxide / CH₂Cl₂ / 12 h / 20 °C

With borane-THF; 7b-Bu-7bH-oxaziridino[2,3-b][1,2]benzisothiazole-3,3-dioxide; mercury(II) trifluoroacetate; sodium hydrogencarbonate; potassium carbonate; dicyclohexyl-carbodiimide; tris-(o-tolyl)phosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; trifluoroacetic acid;
DOI:10.1021/jo0264980