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

Base Information

Chemical Name:methyl (2S,9R,9aS,αR)-9-hydroxy-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-2,3,9,9a-tetrahydro-1H-imidazo(1,2-a)indole-9-propanoate
CAS No.:422319-39-9
Molecular Formula:C₂₆H₂₆Cl₃N₃O₈
Molecular Weight:614.867
Hs Code.:

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

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

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

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

There total 10 articles about methyl (2S,9R,9aS,αR)-9-hydroxy-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-2,3,9,9a-tetrahydro-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: 81.0%

: 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

: 316828-47-4
C₂₅H₂₂Cl₃N₃O₇

: 422319-39-9
methyl (2S,9R,9aS,αR)-9-hydroxy-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-2,3,9,9a-tetrahydro-1H-imidazo(1,2-a)indole-9-propanoate

Guidance literature:: With sodium tetrahydroborate; acetic acid; at 25 ℃; for 2h;
DOI:10.1021/jo0264980

Reference yield: 52.0%

: 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

: 422319-39-9
methyl (2S,9R,9aS,αR)-9-hydroxy-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-2,3,9,9a-tetrahydro-1H-imidazo(1,2-a)indole-9-propanoate

: 422319-37-7
methyl (2S,9S,9aR,αR)-9-hydroxy-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-2,3,9,9a-tetrahydro-1H-imidazo(1,2-a)indole-9-propanoate

Guidance literature:: 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; With oxyaziridine;

With methanol;

With sodium tetrahydroborate; acetic acid; Further stages.;
DOI:10.1021/ol017215d

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

: 422319-39-9
methyl (2S,9R,9aS,αR)-9-hydroxy-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-2,3,9,9a-tetrahydro-1H-imidazo(1,2-a)indole-9-propanoate

Guidance literature:: Multi-step reaction with 8 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: 23 percent / 7b-Bu-7bH-oxaziridino[2,3-b][1,2]benzisothiazole-3,3-dioxide / CH₂Cl₂ / 12 h / 20 °C

8.1: 81 percent / NaBH₄; AcOH / 2 h / 25 °C

With sodium tetrahydroborate; borane-THF; 7b-Bu-7bH-oxaziridino[2,3-b][1,2]benzisothiazole-3,3-dioxide; mercury(II) trifluoroacetate; sodium hydrogencarbonate; potassium carbonate; acetic acid; 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