1-benzyl-N-((1S,2R)-2-((tert-butyldimethylsilyl)oxy)-1-(1,3,4-oxadiazol-2-yl)propyl)-2-(1-hydroxyethyl)pyrrolidine-2-carboxamide

Base Information

Chemical Name:1-benzyl-N-((1S,2R)-2-((tert-butyldimethylsilyl)oxy)-1-(1,3,4-oxadiazol-2-yl)propyl)-2-(1-hydroxyethyl)pyrrolidine-2-carboxamide
CAS No.:1621508-54-0
Molecular Formula:C₂₅H₄₀N₄O₄Si
Molecular Weight:488.702
Hs Code.:

Synonyms:1-benzyl-N-((1S,2R)-2-((tert-butyldimethylsilyl)oxy)-1-(1,3,4-oxadiazol-2-yl)propyl)-2-(1-hydroxyethyl)pyrrolidine-2-carboxamide

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Chemical Property of 1-benzyl-N-((1S,2R)-2-((tert-butyldimethylsilyl)oxy)-1-(1,3,4-oxadiazol-2-yl)propyl)-2-(1-hydroxyethyl)pyrrolidine-2-carboxamide

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Technology Process of 1-benzyl-N-((1S,2R)-2-((tert-butyldimethylsilyl)oxy)-1-(1,3,4-oxadiazol-2-yl)propyl)-2-(1-hydroxyethyl)pyrrolidine-2-carboxamide

There total 8 articles about 1-benzyl-N-((1S,2R)-2-((tert-butyldimethylsilyl)oxy)-1-(1,3,4-oxadiazol-2-yl)propyl)-2-(1-hydroxyethyl)pyrrolidine-2-carboxamide 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: 24.0%

: 1621508-26-6
(1S,2R)-2-((tert-butyldimethylsilyl)oxy)-1-(1,3,4-oxadiazol-2-yl)propan-1-amine

: 1621508-48-2
1-benzyl-2-(1-hydroxyethyl)pyrrolidine-2-carboxylic acid

: 1621508-54-0
1-benzyl-N-((1S,2R)-2-((tert-butyldimethylsilyl)oxy)-1-(1,3,4-oxadiazol-2-yl)propyl)-2-(1-hydroxyethyl)pyrrolidine-2-carboxamide

Guidance literature:: With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 16h;

Reference yield:

: 113304-84-0,127986-89-4
N-benzyl-(S)-proline methyl ester

: 1621508-54-0
1-benzyl-N-((1S,2R)-2-((tert-butyldimethylsilyl)oxy)-1-(1,3,4-oxadiazol-2-yl)propyl)-2-(1-hydroxyethyl)pyrrolidine-2-carboxamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -20 °C

1.2: 3 h / -20 °C

2.1: sodium hydroxide; water / tetrahydrofuran; methanol / 1 h / 95 °C

3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C

With water; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

Reference yield:

: 147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7
L-proline

: 1621508-54-0
1-benzyl-N-((1S,2R)-2-((tert-butyldimethylsilyl)oxy)-1-(1,3,4-oxadiazol-2-yl)propyl)-2-(1-hydroxyethyl)pyrrolidine-2-carboxamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: thionyl chloride / 12 h / 0 °C / Reflux

2.1: triethylamine / dichloromethane / 24 h / 0 - 20 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -20 °C

3.2: 3 h / -20 °C

4.1: sodium hydroxide; water / tetrahydrofuran; methanol / 1 h / 95 °C

5.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C

With thionyl chloride; water; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;