((R)-2-{(S)-2-[(6-Cyano-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-1-cyclohexylmethyl-2-oxo-ethylamino)-acetic acid tert-butyl ester

Base Information

Chemical Name:((R)-2-{(S)-2-[(6-Cyano-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-1-cyclohexylmethyl-2-oxo-ethylamino)-acetic acid tert-butyl ester
CAS No.:182291-42-5
Molecular Formula:C₂₇H₃₇N₅O₄
Molecular Weight:495.622
Hs Code.:

Synonyms:((R)-2-{(S)-2-[(6-Cyano-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-1-cyclohexylmethyl-2-oxo-ethylamino)-acetic acid tert-butyl ester

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Chemical Property of ((R)-2-{(S)-2-[(6-Cyano-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-1-cyclohexylmethyl-2-oxo-ethylamino)-acetic acid tert-butyl ester

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Technology Process of ((R)-2-{(S)-2-[(6-Cyano-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-1-cyclohexylmethyl-2-oxo-ethylamino)-acetic acid tert-butyl ester

There total 18 articles about ((R)-2-{(S)-2-[(6-Cyano-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-1-cyclohexylmethyl-2-oxo-ethylamino)-acetic 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: 97.0%

: (S)-1-((R)-2-Amino-3-cyclohexyl-propionyl)-2,5-dihydro-1H-pyrrole-2-carboxylic acid (6-cyano-pyridin-3-ylmethyl)-amide; hydrochloride

: 5292-43-3
bromoacetic acid tert-butyl ester

: 182291-42-5
((R)-2-{(S)-2-[(6-Cyano-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-1-cyclohexylmethyl-2-oxo-ethylamino)-acetic acid tert-butyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;
DOI:10.1055/s-2004-831200

Reference yield:

: 67515-95-1
5-chlorocarbonyl-pyridine-2-carboxylic acid ethyl ester

: 182291-42-5
((R)-2-{(S)-2-[(6-Cyano-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-1-cyclohexylmethyl-2-oxo-ethylamino)-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: NH₃ / tetrahydrofuran / -10 °C

2: (CF₃CO)2); i-Pr₂NEt / CH₂Cl₂ / 20 °C

3: NH₃ / ethanol / -10 °C

4: 93 percent / aq. HCl; H₂ / Pd/C / propan-1-ol / 6 h / 1500.12 Torr

5: 5 - 20 °C

6: 85 percent / NaBH₄ / aq. ethanol / Heating

7: 74 percent / NaIO₄; AcOH / acetic acid; methanol / 5 °C

8: 95 percent / HCl / ethanol / 0 - 20 °C

9: 75 percent / i-Pr₂NEt; propane phosphonic acid anhydride / CH₂Cl₂; ethyl acetate / 0 - 5 °C

10: 98 percent / (CF₃CO)2O; i-Pr₂NEt / CH₂Cl₂ / 0 - 5 °C

11: 95 percent / HCl / diethyl ether; CH₂Cl₂

12: 97 percent / i-Pr₂NEt / CH₂Cl₂ / 20 °C

With hydrogenchloride; sodium tetrahydroborate; sodium periodate; 1,1,1,4,4,4-hexafluoro-2,3-butanedione; propylphosphonic anhydride; ammonia; hydrogen; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; palladium on activated charcoal; In tetrahydrofuran; methanol; propan-1-ol; diethyl ether; ethanol; dichloromethane; acetic acid; ethyl acetate;
DOI:10.1055/s-2004-831200

Reference yield:

: 5-carbamoyl-pyridine-2-carboxylic acid ethyl ester

: 182291-42-5
((R)-2-{(S)-2-[(6-Cyano-pyridin-3-ylmethyl)-carbamoyl]-2,5-dihydro-pyrrol-1-yl}-1-cyclohexylmethyl-2-oxo-ethylamino)-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: (CF₃CO)2); i-Pr₂NEt / CH₂Cl₂ / 20 °C

2: NH₃ / ethanol / -10 °C

3: 93 percent / aq. HCl; H₂ / Pd/C / propan-1-ol / 6 h / 1500.12 Torr

4: 5 - 20 °C

5: 85 percent / NaBH₄ / aq. ethanol / Heating

6: 74 percent / NaIO₄; AcOH / acetic acid; methanol / 5 °C

7: 95 percent / HCl / ethanol / 0 - 20 °C

8: 75 percent / i-Pr₂NEt; propane phosphonic acid anhydride / CH₂Cl₂; ethyl acetate / 0 - 5 °C

9: 98 percent / (CF₃CO)2O; i-Pr₂NEt / CH₂Cl₂ / 0 - 5 °C

10: 95 percent / HCl / diethyl ether; CH₂Cl₂

11: 97 percent / i-Pr₂NEt / CH₂Cl₂ / 20 °C

With hydrogenchloride; sodium tetrahydroborate; sodium periodate; 1,1,1,4,4,4-hexafluoro-2,3-butanedione; propylphosphonic anhydride; ammonia; hydrogen; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; palladium on activated charcoal; In methanol; propan-1-ol; diethyl ether; ethanol; dichloromethane; acetic acid; ethyl acetate;
DOI:10.1055/s-2004-831200