(S)-5-[3-(1-tert-butoxycarbonyl-3-formylindol-4-yl)benzyl]-2-[(1-tert-butoxycarbonylamino)-2-methylpropyl]oxazole-4-carboxamide

Base Information

Chemical Name:(S)-5-[3-(1-tert-butoxycarbonyl-3-formylindol-4-yl)benzyl]-2-[(1-tert-butoxycarbonylamino)-2-methylpropyl]oxazole-4-carboxamide
CAS No.:866270-11-3
Molecular Formula:C₃₄H₄₀N₄O₇
Molecular Weight:616.714
Hs Code.:

Synonyms:(S)-5-[3-(1-tert-butoxycarbonyl-3-formylindol-4-yl)benzyl]-2-[(1-tert-butoxycarbonylamino)-2-methylpropyl]oxazole-4-carboxamide

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Chemical Property of (S)-5-[3-(1-tert-butoxycarbonyl-3-formylindol-4-yl)benzyl]-2-[(1-tert-butoxycarbonylamino)-2-methylpropyl]oxazole-4-carboxamide

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Technology Process of (S)-5-[3-(1-tert-butoxycarbonyl-3-formylindol-4-yl)benzyl]-2-[(1-tert-butoxycarbonylamino)-2-methylpropyl]oxazole-4-carboxamide

There total 13 articles about (S)-5-[3-(1-tert-butoxycarbonyl-3-formylindol-4-yl)benzyl]-2-[(1-tert-butoxycarbonylamino)-2-methylpropyl]oxazole-4-carboxamide 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: 56.0%

: 866270-06-6
1-tert-butoxycarbonyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)indole-3-carboxaldehyde

: 866270-10-2
(S)-2-[1-(tert-butoxycarbonylamino)-2-methylpropyl]-5-(3-bromobenzyl)oxazole-4-carboxamide

: 866270-11-3
(S)-5-[3-(1-tert-butoxycarbonyl-3-formylindol-4-yl)benzyl]-2-[(1-tert-butoxycarbonylamino)-2-methylpropyl]oxazole-4-carboxamide

Guidance literature:: With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate; In 1,2-dimethoxyethane; at 85 ℃; for 20h;
DOI:10.1021/jo0509760

Reference yield:

: 1878-67-7
3-Bromophenylacetic acid

: 866270-11-3
(S)-5-[3-(1-tert-butoxycarbonyl-3-formylindol-4-yl)benzyl]-2-[(1-tert-butoxycarbonylamino)-2-methylpropyl]oxazole-4-carboxamide

Guidance literature:: Multi-step reaction with 9 steps

1: thionyl chloride / toluene / 1 h / Heating

2: 4.9 g / Et₃N / CH₂Cl₂ / 20 °C

3: LiAlH₄ / diethyl ether / 0.5 h / 0 °C

4: 71 percent / SnCl₂ / CH₂Cl₂ / 4 h

5: 92 percent / 4-acetamidobenzenesulfonyl azide / acetonitrile / 16 h / 20 °C

6: 73 percent / dirhodium tetraoctanoate / CH₂Cl₂ / Heating

7: 65 percent / triphenylphosphine; iodine; Et₃N / CH₂Cl₂ / 16 h

8: 68 percent / NH₃ / ethanol

9: 56 percent / K₂CO₃; PdCl₂(dppf)*CH₂Cl₂ / 1,2-dimethoxy-ethane / 20 h / 85 °C

With lithium aluminium tetrahydride; thionyl chloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; rhodium (II) octanoate dimer; 4-acetamidobenzenesulfonyl azide; ammonia; iodine; potassium carbonate; triethylamine; triphenylphosphine; tin(ll) chloride; In 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; toluene; acetonitrile; 7: Robinson-Gabriel cyclodehydration reaction / 9: Suzuki coupling;
DOI:10.1021/jo0509760

Reference yield:

: 866270-03-3
2-(3-bromophenyl)-N-methoxy-N-methylacetamide

: 866270-11-3
(S)-5-[3-(1-tert-butoxycarbonyl-3-formylindol-4-yl)benzyl]-2-[(1-tert-butoxycarbonylamino)-2-methylpropyl]oxazole-4-carboxamide

Guidance literature:: Multi-step reaction with 7 steps

1: LiAlH₄ / diethyl ether / 0.5 h / 0 °C

2: 71 percent / SnCl₂ / CH₂Cl₂ / 4 h

3: 92 percent / 4-acetamidobenzenesulfonyl azide / acetonitrile / 16 h / 20 °C

4: 73 percent / dirhodium tetraoctanoate / CH₂Cl₂ / Heating

5: 65 percent / triphenylphosphine; iodine; Et₃N / CH₂Cl₂ / 16 h

6: 68 percent / NH₃ / ethanol

7: 56 percent / K₂CO₃; PdCl₂(dppf)*CH₂Cl₂ / 1,2-dimethoxy-ethane / 20 h / 85 °C

With lithium aluminium tetrahydride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; rhodium (II) octanoate dimer; 4-acetamidobenzenesulfonyl azide; ammonia; iodine; potassium carbonate; triethylamine; triphenylphosphine; tin(ll) chloride; In 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; acetonitrile; 5: Robinson-Gabriel cyclodehydration reaction / 7: Suzuki coupling;
DOI:10.1021/jo0509760