{3-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-6-chloro-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-9-yl]-propyl}-carbamic acid benzyl ester

Base Information

Chemical Name:{3-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-6-chloro-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-9-yl]-propyl}-carbamic acid benzyl ester
CAS No.:183794-44-7
Molecular Formula:C₃₃H₃₈ClN₃O₅
Molecular Weight:592.135
Hs Code.:

Synonyms:{3-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-6-chloro-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-9-yl]-propyl}-carbamic acid benzyl ester

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Chemical Property of {3-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-6-chloro-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-9-yl]-propyl}-carbamic acid benzyl ester

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Technology Process of {3-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-6-chloro-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-9-yl]-propyl}-carbamic acid benzyl ester

There total 23 articles about {3-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-6-chloro-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-9-yl]-propyl}-carbamic acid benzyl 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:

: 21887-64-9
N₂-(tert-butoxycarbonyl)-L-ornithine

: 183794-44-7
{3-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-6-chloro-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-9-yl]-propyl}-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) Me₄NOH / 1.) MeOH, EtOH, 2.) DMF, 3 h

2: 93 percent / SOCl₂ / 23 h / Ambient temperature

3: 84 percent / triethylamine / dimethylformamide / 2.5 h / 0 °C

4: 97 percent / aq. LiOH / tetrahydrofuran / 2.5 h / Ambient temperature

5: 66 percent / PCl₅ / tetrahydrofuran / 1.75 h / 0 °C

6: 82 percent / Bu₄NF / tetrahydrofuran / 0.5 h

7: 94 percent / triethylamine / CH₂Cl₂ / 1.5 h / Ambient temperature

8: 57 percent / NaH / dimethylsulfoxide / 2 h

9: 100 percent / H₂, HOAc / Pd / ethanol; H₂O; methanol / 48 h

10: 87 percent / NaHCO₃ / tetrahydrofuran; H₂O / 18 h

11: 90 percent / K₂CO₃ / CHCl₃; methanol / 37 h / Heating

12: 1.) Bu₄NF, 2.) NaBH₄ / 1.) THF, 2 h, 2.) THF, CH₃OH, 1 h

With lithium hydroxide; sodium tetrahydroborate; thionyl chloride; phosphorus pentachloride; tetramethyl ammoniumhydroxide; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; palladium; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo961114p

Reference yield:

: 183794-28-7
{(2R,3S)-3-[(S)-2-Amino-3-(4-benzyloxy-phenyl)-propoxymethyl]-oxiranyl}-methanol

: 183794-44-7
{3-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-6-chloro-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-9-yl]-propyl}-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 72 percent / dioxane / 9 h / Heating

2: 80 percent / triethylamine / CH₂Cl₂ / 1.17 h

3: 99 percent / collidine / CH₂Cl₂ / 1.25 h

4: 79 percent / triethylamine / acetonitrile / 10 h / Heating

5: 66 percent / PCl₅ / tetrahydrofuran / 1.75 h / 0 °C

6: 82 percent / Bu₄NF / tetrahydrofuran / 0.5 h

7: 94 percent / triethylamine / CH₂Cl₂ / 1.5 h / Ambient temperature

8: 57 percent / NaH / dimethylsulfoxide / 2 h

9: 100 percent / H₂, HOAc / Pd / ethanol; H₂O; methanol / 48 h

10: 87 percent / NaHCO₃ / tetrahydrofuran; H₂O / 18 h

11: 90 percent / K₂CO₃ / CHCl₃; methanol / 37 h / Heating

12: 1.) Bu₄NF, 2.) NaBH₄ / 1.) THF, 2 h, 2.) THF, CH₃OH, 1 h

With 2,3,5-trimethyl-pyridine; sodium tetrahydroborate; phosphorus pentachloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; palladium; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; chloroform; water; dimethyl sulfoxide; acetonitrile;
DOI:10.1021/jo961114p

Reference yield:

: 183794-30-1
Methanesulfonic acid (S)-2-[(3R,5S)-5-(4-benzyloxy-benzyl)-morpholin-3-yl]-2-hydroxy-ethyl ester

: 183794-44-7
{3-[(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-6-chloro-10-oxo-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-9-yl]-propyl}-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 99 percent / collidine / CH₂Cl₂ / 1.25 h

2: 79 percent / triethylamine / acetonitrile / 10 h / Heating

3: 66 percent / PCl₅ / tetrahydrofuran / 1.75 h / 0 °C

4: 82 percent / Bu₄NF / tetrahydrofuran / 0.5 h

5: 94 percent / triethylamine / CH₂Cl₂ / 1.5 h / Ambient temperature

6: 57 percent / NaH / dimethylsulfoxide / 2 h

7: 100 percent / H₂, HOAc / Pd / ethanol; H₂O; methanol / 48 h

8: 87 percent / NaHCO₃ / tetrahydrofuran; H₂O / 18 h

9: 90 percent / K₂CO₃ / CHCl₃; methanol / 37 h / Heating

10: 1.) Bu₄NF, 2.) NaBH₄ / 1.) THF, 2 h, 2.) THF, CH₃OH, 1 h

With 2,3,5-trimethyl-pyridine; sodium tetrahydroborate; phosphorus pentachloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; palladium; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; dimethyl sulfoxide; acetonitrile;
DOI:10.1021/jo961114p