(S)-benzyl 5-{3-[3-(2-benzyloxycarbonylaminoethyl)-1H-indol-4-yl]-benzyl}-2-(1-tert-butoxycarbonylamino-2-methylpropyl)oxazole-4-carboxylate

Base Information

Chemical Name:(S)-benzyl 5-{3-[3-(2-benzyloxycarbonylaminoethyl)-1H-indol-4-yl]-benzyl}-2-(1-tert-butoxycarbonylamino-2-methylpropyl)oxazole-4-carboxylate
CAS No.:866270-25-9
Molecular Formula:C₄₅H₄₈N₄O₇
Molecular Weight:756.899
Hs Code.:

Synonyms:(S)-benzyl 5-{3-[3-(2-benzyloxycarbonylaminoethyl)-1H-indol-4-yl]-benzyl}-2-(1-tert-butoxycarbonylamino-2-methylpropyl)oxazole-4-carboxylate

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Chemical Property of (S)-benzyl 5-{3-[3-(2-benzyloxycarbonylaminoethyl)-1H-indol-4-yl]-benzyl}-2-(1-tert-butoxycarbonylamino-2-methylpropyl)oxazole-4-carboxylate

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Technology Process of (S)-benzyl 5-{3-[3-(2-benzyloxycarbonylaminoethyl)-1H-indol-4-yl]-benzyl}-2-(1-tert-butoxycarbonylamino-2-methylpropyl)oxazole-4-carboxylate

There total 14 articles about (S)-benzyl 5-{3-[3-(2-benzyloxycarbonylaminoethyl)-1H-indol-4-yl]-benzyl}-2-(1-tert-butoxycarbonylamino-2-methylpropyl)oxazole-4-carboxylate 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:

: 866270-07-7
4-bromo-N²-carboxybenzylaminotryptamine

: 866270-25-9
(S)-benzyl 5-{3-[3-(2-benzyloxycarbonylaminoethyl)-1H-indol-4-yl]-benzyl}-2-(1-tert-butoxycarbonylamino-2-methylpropyl)oxazole-4-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: potassium acetate; Et₃N; palladium acetate / 2-(dicyclohexylphosphino)biphenyl / dioxane / 0.75 h / 70 °C

2: 105 mg / K₂CO₃; PdCl₂(dppf)*CH₂Cl₂ / 1,2-dimethoxy-ethane / 3 h / 85 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; palladium diacetate; potassium carbonate; triethylamine; CyJohnPhos; In 1,4-dioxane; 1,2-dimethoxyethane; 2: Suzuki coupling;
DOI:10.1021/jo0509760

Reference yield:

: 98600-34-1
4-bromo-1H-indole-3-carbaldehyde

: 866270-25-9
(S)-benzyl 5-{3-[3-(2-benzyloxycarbonylaminoethyl)-1H-indol-4-yl]-benzyl}-2-(1-tert-butoxycarbonylamino-2-methylpropyl)oxazole-4-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 77 percent / NH₄OAc / 3 h / Heating

2: LiAlH₄ / tetrahydrofuran / 4 h / Heating

3: 819 mg / K₂CO₃ / ethyl acetate; H₂O / 1 h

4: potassium acetate; Et₃N; palladium acetate / 2-(dicyclohexylphosphino)biphenyl / dioxane / 0.75 h / 70 °C

5: 105 mg / K₂CO₃; PdCl₂(dppf)*CH₂Cl₂ / 1,2-dimethoxy-ethane / 3 h / 85 °C

With lithium aluminium tetrahydride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; ammonium acetate; potassium acetate; palladium diacetate; potassium carbonate; triethylamine; CyJohnPhos; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; water; ethyl acetate; 5: Suzuki coupling;
DOI:10.1021/jo0509760

Reference yield:

: 108061-74-1
2-(4-bromo-1H-indol-3-yl)ethan-1-amine

: 866270-25-9
(S)-benzyl 5-{3-[3-(2-benzyloxycarbonylaminoethyl)-1H-indol-4-yl]-benzyl}-2-(1-tert-butoxycarbonylamino-2-methylpropyl)oxazole-4-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 819 mg / K₂CO₃ / ethyl acetate; H₂O / 1 h

2: potassium acetate; Et₃N; palladium acetate / 2-(dicyclohexylphosphino)biphenyl / dioxane / 0.75 h / 70 °C

3: 105 mg / K₂CO₃; PdCl₂(dppf)*CH₂Cl₂ / 1,2-dimethoxy-ethane / 3 h / 85 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; palladium diacetate; potassium carbonate; triethylamine; CyJohnPhos; In 1,4-dioxane; 1,2-dimethoxyethane; water; ethyl acetate; 3: Suzuki coupling;
DOI:10.1021/jo0509760