Technology Process of (2-{[(1S,4S,8R)-10-((2R,8S)-8-Benzyl-4-oxo-1,2,3,4,5,6,7,8-octahydro-quinoline-2-carbonyl)-6-oxo-3,10-diaza-tricyclo[6.2.1.02,7]undec-2(7)-ene-4-carbonyl]-amino}-ethyl)-carbamic acid tert-butyl ester
There total 11 articles about (2-{[(1S,4S,8R)-10-((2R,8S)-8-Benzyl-4-oxo-1,2,3,4,5,6,7,8-octahydro-quinoline-2-carbonyl)-6-oxo-3,10-diaza-tricyclo[6.2.1.02,7]undec-2(7)-ene-4-carbonyl]-amino}-ethyl)-carbamic acid tert-butyl ester which
guide to synthetic route it.
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synthetic route:
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177723-63-6
(2-{[(1S,4S,8R)-10-((2R,8S)-8-Benzyl-4-oxo-1,2,3,4,5,6,7,8-octahydro-quinoline-2-carbonyl)-6-oxo-3,10-diaza-tricyclo[6.2.1.02,7]undec-2(7)-ene-4-carbonyl]-amino}-ethyl)-carbamic acid tert-butyl ester
- Guidance literature:
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Multi-step reaction with 4 steps
1: 71 percent / EDC, HOBT, Et3N / CH2Cl2 / 15 h / Ambient temperature
2: 50 percent / Pd/C / cyclohexene; methanol / 0.33 h / Heating
3: H2 / Pd/C / methanol / 24 h / 760 Torr
4: 35 mg / EDC, HOBT, Et3N / CH2Cl2 / 24 h
With
hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine;
palladium on activated charcoal;
In
methanol; dichloromethane; cyclohexene;
DOI:10.1021/jo9522771
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177723-63-6
(2-{[(1S,4S,8R)-10-((2R,8S)-8-Benzyl-4-oxo-1,2,3,4,5,6,7,8-octahydro-quinoline-2-carbonyl)-6-oxo-3,10-diaza-tricyclo[6.2.1.02,7]undec-2(7)-ene-4-carbonyl]-amino}-ethyl)-carbamic acid tert-butyl ester
- Guidance literature:
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Multi-step reaction with 9 steps
1: 1.) BH3*THF, 2.) H2O2, NaOH / 1.) THF, rt, 1 h, 2.) THF, H2O, rt, 45 min
2: oxalyl chloride, DMSO / CH2Cl2; diethyl ether
3: KHMDS / 1.) THF, -78 deg C, 30 min, 2.) 10 min
4: 1.) MeLi / 1.) THF, Et2O, -10 deg C, 10 min, 2.) rt, 30 min
5: 398 mg / KOH / tetrahydrofuran; H2O / 1 h / Ambient temperature
6: 71 percent / EDC, HOBT, Et3N / CH2Cl2 / 15 h / Ambient temperature
7: 50 percent / Pd/C / cyclohexene; methanol / 0.33 h / Heating
8: H2 / Pd/C / methanol / 24 h / 760 Torr
9: 35 mg / EDC, HOBT, Et3N / CH2Cl2 / 24 h
With
potassium hydroxide; sodium hydroxide; borane-THF; oxalyl dichloride; methyllithium; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; benzotriazol-1-ol; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; cyclohexene;
DOI:10.1021/jo9522771
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-
177723-63-6
(2-{[(1S,4S,8R)-10-((2R,8S)-8-Benzyl-4-oxo-1,2,3,4,5,6,7,8-octahydro-quinoline-2-carbonyl)-6-oxo-3,10-diaza-tricyclo[6.2.1.02,7]undec-2(7)-ene-4-carbonyl]-amino}-ethyl)-carbamic acid tert-butyl ester
- Guidance literature:
-
Multi-step reaction with 7 steps
1: KHMDS / 1.) THF, -78 deg C, 30 min, 2.) 10 min
2: 1.) MeLi / 1.) THF, Et2O, -10 deg C, 10 min, 2.) rt, 30 min
3: 398 mg / KOH / tetrahydrofuran; H2O / 1 h / Ambient temperature
4: 71 percent / EDC, HOBT, Et3N / CH2Cl2 / 15 h / Ambient temperature
5: 50 percent / Pd/C / cyclohexene; methanol / 0.33 h / Heating
6: H2 / Pd/C / methanol / 24 h / 760 Torr
7: 35 mg / EDC, HOBT, Et3N / CH2Cl2 / 24 h
With
potassium hydroxide; methyllithium; hydrogen; potassium hexamethylsilazane; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; water; cyclohexene;
DOI:10.1021/jo9522771