(2-{[(1S,4S,8R)-6-Oxo-10-((R)-1-phenyl-ethyl)-3,10-diaza-tricyclo[6.2.1.0^2,7]undec-2⁽⁷⁾-ene-4-carbonyl]-amino}-ethyl)-carbamic acid tert-butyl ester

Base Information

• Chemical Name: (2-{[(1S,4S,8R)-6-Oxo-10-((R)-1-phenyl-ethyl)-3,10-diaza-tricyclo[6.2.1.0^2,7]undec-2⁽⁷⁾-ene-4-carbonyl]-amino}-ethyl)-carbamic acid tert-butyl ester
• CAS No.: 177723-62-5
• Molecular Formula: C₂₅H₃₄N₄O₄
• Molecular Weight: 454.569

Synonyms:(2-{[(1S,4S,8R)-6-Oxo-10-((R)-1-phenyl-ethyl)-3,10-diaza-tricyclo[6.2.1.0^2,7]undec-2⁽⁷⁾-ene-4-carbonyl]-amino}-ethyl)-carbamic acid tert-butyl ester

Chemical Property of (2-{[(1S,4S,8R)-6-Oxo-10-((R)-1-phenyl-ethyl)-3,10-diaza-tricyclo[6.2.1.0^2,7]undec-2⁽⁷⁾-ene-4-carbonyl]-amino}-ethyl)-carbamic acid tert-butyl ester

Chemical Property:

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Technology Process of (2-{[(1S,4S,8R)-6-Oxo-10-((R)-1-phenyl-ethyl)-3,10-diaza-tricyclo[6.2.1.0^2,7]undec-2⁽⁷⁾-ene-4-carbonyl]-amino}-ethyl)-carbamic acid tert-butyl ester

There total 11 articles about (2-{[(1S,4S,8R)-6-Oxo-10-((R)-1-phenyl-ethyl)-3,10-diaza-tricyclo[6.2.1.0^2,7]undec-2⁽⁷⁾-ene-4-carbonyl]-amino}-ethyl)-carbamic acid tert-butyl 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: 50.0%

{(S)-1-(2-tert-Butoxycarbonylamino-ethylcarbamoyl)-3-oxo-3-[(1S,4R)-6-oxo-2-((R)-1-phenyl-ethyl)-2-aza-bicyclo[2.2.1]hept-5-yl]-propyl}-carbamic acid benzyl ester → (2-{[(1S,4S,8R)-6-Oxo-10-((R)-1-phenyl-ethyl)-3,10-diaza-tricyclo[6.2.1.02,7]undec-2(7)-ene-4-carbonyl]-amino}-ethyl)-carbamic acid tert-butyl ester (177723-62-5)

Guidance literature:

palladium on activated charcoal; In methanol; cyclohexene; for 0.333333h; Heating;

DOI:10.1021/jo9522771

Reference yield:

N-BOC-1,2-diaminoethane (57260-73-8) → (2-{[(1S,4S,8R)-6-Oxo-10-((R)-1-phenyl-ethyl)-3,10-diaza-tricyclo[6.2.1.02,7]undec-2(7)-ene-4-carbonyl]-amino}-ethyl)-carbamic acid tert-butyl ester (177723-62-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / EDC, HOBT, Et₃N / CH₂Cl₂ / 15 h / Ambient temperature

2: 50 percent / Pd/C / cyclohexene; methanol / 0.33 h / Heating

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; cyclohexene;

DOI:10.1021/jo9522771

Reference yield:

(R)-1-phenyl-ethyl-amine (3886-69-9) → (2-{[(1S,4S,8R)-6-Oxo-10-((R)-1-phenyl-ethyl)-3,10-diaza-tricyclo[6.2.1.02,7]undec-2(7)-ene-4-carbonyl]-amino}-ethyl)-carbamic acid tert-butyl ester (177723-62-5)

Guidance literature:

Multi-step reaction with 9 steps

1: HCl / H₂O

2: 13.7 g / HCl / H₂O / 0 °C

3: 1.) BH₃*THF, 2.) H₂O₂, NaOH / 1.) THF, rt, 1 h, 2.) THF, H₂O, rt, 45 min

4: oxalyl chloride, DMSO / CH₂Cl₂; diethyl ether

5: KHMDS / 1.) THF, -78 deg C, 30 min, 2.) 10 min

6: 1.) MeLi / 1.) THF, Et₂O, -10 deg C, 10 min, 2.) rt, 30 min

7: 398 mg / KOH / tetrahydrofuran; H₂O / 1 h / Ambient temperature

8: 71 percent / EDC, HOBT, Et₃N / CH₂Cl₂ / 15 h / Ambient temperature

9: 50 percent / Pd/C / cyclohexene; methanol / 0.33 h / Heating

With hydrogenchloride; potassium hydroxide; sodium hydroxide; borane-THF; oxalyl dichloride; methyllithium; 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

upstream raw materials:

N-BOC-1,2-diaminoethane

(R)-1-phenyl-ethyl-amine

(-)-(1S,1'R)-2-(1'-Phenylethyl)-2-azabicyclo<2.2.1>hept-5-ene

1-phenethyl-3-oxo-1-azabicyclo[2.2.1]heptane

Downstream raw materials:

(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[6.2.1.0^2,7]undec-2⁽⁷⁾-ene-4-carbonyl]-amino}-ethyl)-carbamic acid tert-butyl ester

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