(2S,9R,9aS)-9-Hydroxy-2-isobutyl-9-[(R)-2-methoxycarbonyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-ethyl]-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,9R,9aS)-9-Hydroxy-2-isobutyl-9-[(R)-2-methoxycarbonyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-ethyl]-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester
• CAS No.: 422319-55-9
• Molecular Formula: C₂₉H₃₂Cl₃N₃O₈
• Molecular Weight: 656.947
• Mol file: 422319-55-9.mol

Synonyms:(2S,9R,9aS)-9-Hydroxy-2-isobutyl-9-[(R)-2-methoxycarbonyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-ethyl]-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

Chemical Property of (2S,9R,9aS)-9-Hydroxy-2-isobutyl-9-[(R)-2-methoxycarbonyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-ethyl]-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,9R,9aS)-9-Hydroxy-2-isobutyl-9-[(R)-2-methoxycarbonyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-ethyl]-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

There total 10 articles about (2S,9R,9aS)-9-Hydroxy-2-isobutyl-9-[(R)-2-methoxycarbonyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-ethyl]-3-oxo-2,3,9,9a-tetrahydro-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: 76.0%

(2S,9R)-9-Hydroxy-2-isobutyl-9a-methoxy-9-[(R)-2-methoxycarbonyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-ethyl]-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester (316828-38-3) → C28H28Cl3N3O7 (316828-41-8) + (2S,9R,9aS)-9-Hydroxy-2-isobutyl-9-[(R)-2-methoxycarbonyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-ethyl]-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester (422319-55-9)

Guidance literature:

With sodium tetrahydroborate; acetic acid; at 25 ℃; for 3h;

DOI:10.1021/jo0264980

Reference yield: 50.0%

methyl (αR,2S)-2,3-dihydro-2-(2-methylpropyl)-3-oxo-1-[(phenylmethoxy)carbonyl]-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1H-imidazo(1,2-a)indole-9-propanoate (316828-34-9) → (2S,9S,9aR)-9-Hydroxy-2-isobutyl-9-[(R)-2-methoxycarbonyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-ethyl]-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester + (2S,9R,9aS)-9-Hydroxy-2-isobutyl-9-[(R)-2-methoxycarbonyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-ethyl]-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester (422319-55-9)

Guidance literature:

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

With methanol;

With sodium tetrahydroborate; acetic acid; Further stages.;

DOI:10.1021/ol017215d

Reference yield:

(R)-(+)-tryptophan methyl ester hydrochloride (14907-27-8,5619-09-0,7524-52-9,26988-71-6,41222-70-2,67557-19-1,109492-62-8) → (2S,9R,9aS)-9-Hydroxy-2-isobutyl-9-[(R)-2-methoxycarbonyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-ethyl]-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester (422319-55-9)

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: 3.64 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: 67 percent / P(o-tolyl)3; K₂CO₃ / Pd₂(dba)3 / toluene / 2 h / 105 °C

7.1: 55 percent / dimethyldioxirane / CH₂Cl₂; acetone / 0.08 h / -78 °C

8.1: 76 percent / NaBH₄; AcOH / 3 h / 25 °C

With sodium tetrahydroborate; borane-THF; mercury(II) trifluoroacetate; 3,3-dimethyldioxirane; 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; acetone; toluene; trifluoroacetic acid;

DOI:10.1021/jo0264980

upstream raw materials:

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

(2S,9R)-9-Hydroxy-2-isobutyl-9a-methoxy-9-[(R)-2-methoxycarbonyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-ethyl]-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

Z-Leu-OH

(R)-(+)-tryptophan methyl ester hydrochloride

Downstream raw materials:

C₆₃H₅₅N₅O₉Se

C₅₆H₅₁N₅O₉Se

C₅₆H₄₉N₅O₈Se

C₃₉H₃₆N₄O₆