3-[2-(1-tert-butoxycarbonylamino-2-oxo-3,3-diphenyl-butyl)-oxazol-5-yl]-indole-1-carboxylic acid ethyl ester

Base Information

Chemical Name:3-[2-(1-tert-butoxycarbonylamino-2-oxo-3,3-diphenyl-butyl)-oxazol-5-yl]-indole-1-carboxylic acid ethyl ester
CAS No.:340983-20-2
Molecular Formula:C₃₅H₃₅N₃O₆
Molecular Weight:593.679
Hs Code.:

Synonyms:3-[2-(1-tert-butoxycarbonylamino-2-oxo-3,3-diphenyl-butyl)-oxazol-5-yl]-indole-1-carboxylic acid ethyl ester

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Chemical Property of 3-[2-(1-tert-butoxycarbonylamino-2-oxo-3,3-diphenyl-butyl)-oxazol-5-yl]-indole-1-carboxylic acid ethyl ester

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Technology Process of 3-[2-(1-tert-butoxycarbonylamino-2-oxo-3,3-diphenyl-butyl)-oxazol-5-yl]-indole-1-carboxylic acid ethyl ester

There total 8 articles about 3-[2-(1-tert-butoxycarbonylamino-2-oxo-3,3-diphenyl-butyl)-oxazol-5-yl]-indole-1-carboxylic acid ethyl 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: 78.0%

: 340983-19-9
3-(2-{[tert-butoxycarbonyl-(2,2-diphenyl-propionyl)-amino]-methyl}-oxazol-5-yl)-indole-1-carboxylic acid ethyl ester

: 340983-20-2
3-[2-(1-tert-butoxycarbonylamino-2-oxo-3,3-diphenyl-butyl)-oxazol-5-yl]-indole-1-carboxylic acid ethyl ester

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;
DOI:10.1021/ol0157196

Reference yield:

: 2-amino-1-(1H-indol-3-yl)ethan-1-one acetate

: 340983-20-2
3-[2-(1-tert-butoxycarbonylamino-2-oxo-3,3-diphenyl-butyl)-oxazol-5-yl]-indole-1-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 66 percent / IBCF; NMM / dimethylformamide / 2 h / -20 °C

2: PPh₃; Et₃N; Cl₃CCCl₃ / CH₂Cl₂ / 1 h

3: 171 mg / Et₃N; DMAP / CH₂Cl₂ / 0.5 h

4: H₂ / Pd/C / ethanol / 4 h / 20 °C

5: 253 mg / PyBOP; i-Pr₂NEt / dimethylformamide / 18 h / 20 °C

6: 42 percent / n-BuLi; DMAP / tetrahydrofuran; hexane / 18 h / 20 °C

7: 78 percent / LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

With 4-methyl-morpholine; dmap; n-butyllithium; hexachloroethane; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium diisopropyl amide; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 7: Chan rearrangement;
DOI:10.1021/ol0157196

Reference yield:

: 1026822-81-0
[5-(1H-indol-3-yl)-oxazol-2-ylmethyl]-carbamic acid benzyl ester

: 340983-20-2
3-[2-(1-tert-butoxycarbonylamino-2-oxo-3,3-diphenyl-butyl)-oxazol-5-yl]-indole-1-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 171 mg / Et₃N; DMAP / CH₂Cl₂ / 0.5 h

2: H₂ / Pd/C / ethanol / 4 h / 20 °C

3: 253 mg / PyBOP; i-Pr₂NEt / dimethylformamide / 18 h / 20 °C

4: 42 percent / n-BuLi; DMAP / tetrahydrofuran; hexane / 18 h / 20 °C

5: 78 percent / LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

With dmap; n-butyllithium; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 5: Chan rearrangement;
DOI:10.1021/ol0157196