(3S,4S,7R,10S)-1-aza-3-pyroglutamoylamino-4-phenyl-10-carbomethoxybicyclo[5.3.0]decane

Base Information

Chemical Name:(3S,4S,7R,10S)-1-aza-3-pyroglutamoylamino-4-phenyl-10-carbomethoxybicyclo[5.3.0]decane
CAS No.:328974-88-5
Molecular Formula:C₂₂H₂₇N₃O₅
Molecular Weight:413.473
Hs Code.:

Synonyms:(3S,4S,7R,10S)-1-aza-3-pyroglutamoylamino-4-phenyl-10-carbomethoxybicyclo[5.3.0]decane

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Chemical Property of (3S,4S,7R,10S)-1-aza-3-pyroglutamoylamino-4-phenyl-10-carbomethoxybicyclo[5.3.0]decane

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Technology Process of (3S,4S,7R,10S)-1-aza-3-pyroglutamoylamino-4-phenyl-10-carbomethoxybicyclo[5.3.0]decane

There total 7 articles about (3S,4S,7R,10S)-1-aza-3-pyroglutamoylamino-4-phenyl-10-carbomethoxybicyclo[5.3.0]decane 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: 70.0%

: 59850-85-0
N-hydroxysuccinimide ester of pyroglutamic acid

: 328974-71-6
(3S,4S,7R,10S)-1-aza-3-t-butoxycarbonylamino-4-phenyl-10-carbomethoxybicyclo[5.3.0]decane

: 328974-88-5
(3S,4S,7R,10S)-1-aza-3-pyroglutamoylamino-4-phenyl-10-carbomethoxybicyclo[5.3.0]decane

Guidance literature:: (3S,4S,7R,10S)-1-aza-3-t-butoxycarbonylamino-4-phenyl-10-carbomethoxybicyclo[5.3.0]decane; With hydrogenchloride; In ethyl acetate; at 20 ℃; for 2h;

N-hydroxysuccinimide ester of pyroglutamic acid; With triethylamine; In dichloromethane; at 20 ℃;
DOI:10.1016/S0040-4020(00)00856-5

Reference yield:

: 185385-13-1
1-carbomethoxy-5-methoxy-L-proline methyl ester

: 328974-88-5
(3S,4S,7R,10S)-1-aza-3-pyroglutamoylamino-4-phenyl-10-carbomethoxybicyclo[5.3.0]decane

Guidance literature:: Multi-step reaction with 6 steps

1.1: 44 percent / SnCl₄; AlCl₃ / CH₂Cl₂ / 36 h / 20 °C

2.1: TBAF / tetrahydrofuran / -20 °C

2.2: H₂ / Lindlar catalyst / ethyl acetate

2.3: TMSI / CHCl₃ / 50 °C

3.1: 75 percent / HOBt; DCC / CH₂Cl₂ / -20 - 20 °C

4.1: 65 percent / bis(tricyclohexylphosphine)-benzylidene ruthenium(IV)Cl₂ / CH₂Cl₂ / 24 h / Heating

5.1: 89 percent / H₂ / Pd/C / methanol

6.1: aq. HCl / ethyl acetate / 2 h / 20 °C

6.2: 70 percent / Et₃N / CH₂Cl₂ / 20 °C

With hydrogenchloride; Grubbs catalyst first generation; aluminium trichloride; tetrabutyl ammonium fluoride; hydrogen; tin(IV) chloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4020(00)00856-5

Reference yield:

: 138958-09-5
cis-N-(methoxycarbonyl)-5-<2-(trimethylsilyl)ethynyl>-L-proline methyl ester

: 328974-88-5
(3S,4S,7R,10S)-1-aza-3-pyroglutamoylamino-4-phenyl-10-carbomethoxybicyclo[5.3.0]decane

Guidance literature:: Multi-step reaction with 5 steps

1.1: TBAF / tetrahydrofuran / -20 °C

1.2: H₂ / Lindlar catalyst / ethyl acetate

1.3: TMSI / CHCl₃ / 50 °C

2.1: 75 percent / HOBt; DCC / CH₂Cl₂ / -20 - 20 °C

3.1: 65 percent / bis(tricyclohexylphosphine)-benzylidene ruthenium(IV)Cl₂ / CH₂Cl₂ / 24 h / Heating

4.1: 89 percent / H₂ / Pd/C / methanol

5.1: aq. HCl / ethyl acetate / 2 h / 20 °C

5.2: 70 percent / Et₃N / CH₂Cl₂ / 20 °C

With hydrogenchloride; Grubbs catalyst first generation; tetrabutyl ammonium fluoride; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4020(00)00856-5