N-[(2R)-t-butoxycarbonylamino-(3R)-phenyl-4-pentenoyl]-(5R)-vinylproline methyl ester

Base Information

Chemical Name:N-[(2R)-t-butoxycarbonylamino-(3R)-phenyl-4-pentenoyl]-(5R)-vinylproline methyl ester
CAS No.:328974-68-1
Molecular Formula:C₂₄H₃₂N₂O₅
Molecular Weight:428.528
Hs Code.:

Synonyms:N-[(2R)-t-butoxycarbonylamino-(3R)-phenyl-4-pentenoyl]-(5R)-vinylproline methyl ester

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Chemical Property of N-[(2R)-t-butoxycarbonylamino-(3R)-phenyl-4-pentenoyl]-(5R)-vinylproline methyl ester

Chemical Property:

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Technology Process of N-[(2R)-t-butoxycarbonylamino-(3R)-phenyl-4-pentenoyl]-(5R)-vinylproline methyl ester

There total 3 articles about N-[(2R)-t-butoxycarbonylamino-(3R)-phenyl-4-pentenoyl]-(5R)-vinylproline methyl 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: 75.0%

: 210345-07-6
5R-vinyl proline methyl ester

: (2R,3R)-2-tert-Butoxycarbonylamino-3-phenyl-pent-4-enoic acid

: 328974-68-1
N-[(2R)-t-butoxycarbonylamino-(3R)-phenyl-4-pentenoyl]-(5R)-vinylproline methyl ester

Guidance literature:: With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; at -20 - 20 ℃;
DOI:10.1016/S0040-4020(00)00856-5

Reference yield:

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

: 328974-68-1
N-[(2R)-t-butoxycarbonylamino-(3R)-phenyl-4-pentenoyl]-(5R)-vinylproline methyl ester

Guidance literature:: Multi-step reaction with 3 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

With aluminium trichloride; tetrabutyl ammonium fluoride; tin(IV) chloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(00)00856-5

Reference yield:

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

: 328974-68-1
N-[(2R)-t-butoxycarbonylamino-(3R)-phenyl-4-pentenoyl]-(5R)-vinylproline methyl ester

Guidance literature:: Multi-step reaction with 2 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

With tetrabutyl ammonium fluoride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(00)00856-5