2-{benzyl[1-tert-butoxycarbonyl-4-(tert-butyldimethylsilanyloxymethyl)-2,3-dihydro-1H-pyrrole-2-carbonyl]amino}malonic acid diethyl ester

Base Information

Chemical Name:2-{benzyl[1-tert-butoxycarbonyl-4-(tert-butyldimethylsilanyloxymethyl)-2,3-dihydro-1H-pyrrole-2-carbonyl]amino}malonic acid diethyl ester
CAS No.:915779-92-9
Molecular Formula:C₃₁H₄₈N₂O₈Si
Molecular Weight:604.816
Hs Code.:

2-{benzyl[1-tert-butoxycarbonyl-4-(tert-butyldimethylsilanyloxymethyl)-2,3-dihydro-1H-pyrrole-2-carbonyl]amino}malonic acid diethyl ester

Synonyms:2-{benzyl[1-tert-butoxycarbonyl-4-(tert-butyldimethylsilanyloxymethyl)-2,3-dihydro-1H-pyrrole-2-carbonyl]amino}malonic acid diethyl ester

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Chemical Property of 2-{benzyl[1-tert-butoxycarbonyl-4-(tert-butyldimethylsilanyloxymethyl)-2,3-dihydro-1H-pyrrole-2-carbonyl]amino}malonic acid diethyl ester

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Technology Process of 2-{benzyl[1-tert-butoxycarbonyl-4-(tert-butyldimethylsilanyloxymethyl)-2,3-dihydro-1H-pyrrole-2-carbonyl]amino}malonic acid diethyl ester

There total 7 articles about 2-{benzyl[1-tert-butoxycarbonyl-4-(tert-butyldimethylsilanyloxymethyl)-2,3-dihydro-1H-pyrrole-2-carbonyl]amino}malonic acid diethyl 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: 76.0%

: 915779-91-8
2-(benzyl-ethoxycarbonylmethyl-carbamoyl)-4-(tert-butyldimethylsilanyloxymethyl)-2,3-dihydropyrrole-1-carboxylic acid tert-butyl ester

: 541-41-3
chloroformic acid ethyl ester

: 915779-92-9
2-{benzyl[1-tert-butoxycarbonyl-4-(tert-butyldimethylsilanyloxymethyl)-2,3-dihydro-1H-pyrrole-2-carbonyl]amino}malonic acid diethyl ester

Guidance literature:: 2-(benzyl-ethoxycarbonylmethyl-carbamoyl)-4-(tert-butyldimethylsilanyloxymethyl)-2,3-dihydropyrrole-1-carboxylic acid tert-butyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1h;

chloroformic acid ethyl ester; In tetrahydrofuran; diethyl ether; at -78 ℃; for 7h;
DOI:10.1016/j.tet.2006.06.114

Reference yield:

: 915779-84-9
4-formyl-2,3-dihydropyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

: 915779-92-9
2-{benzyl[1-tert-butoxycarbonyl-4-(tert-butyldimethylsilanyloxymethyl)-2,3-dihydro-1H-pyrrole-2-carbonyl]amino}malonic acid diethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 99 percent / NaBH₄ / CH₂Cl₂; methanol / 2 h / -78 - 0 °C

2.1: 83 percent / triethylamine; DMAP / CH₂Cl₂ / 10 h / 20 °C

3.1: 68 percent / LiOH / methanol; H₂O / 10 h / 20 °C

4.1: 78 percent / 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; triethylamine / CH₂Cl₂ / 4 h / 20 °C

5.1: LHMDS / diethyl ether; tetrahydrofuran / 1 h / -78 °C

5.2: 76 percent / diethyl ether; tetrahydrofuran / 7 h / -78 °C

With dmap; lithium hydroxide; sodium tetrahydroborate; triethylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;
DOI:10.1016/j.tet.2006.06.114

Reference yield:

: 915779-99-6
4-hydroxymethyl-2,3-dihydropyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

: 915779-92-9
2-{benzyl[1-tert-butoxycarbonyl-4-(tert-butyldimethylsilanyloxymethyl)-2,3-dihydro-1H-pyrrole-2-carbonyl]amino}malonic acid diethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 83 percent / triethylamine; DMAP / CH₂Cl₂ / 10 h / 20 °C

2.1: 68 percent / LiOH / methanol; H₂O / 10 h / 20 °C

3.1: 78 percent / 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; triethylamine / CH₂Cl₂ / 4 h / 20 °C

4.1: LHMDS / diethyl ether; tetrahydrofuran / 1 h / -78 °C

4.2: 76 percent / diethyl ether; tetrahydrofuran / 7 h / -78 °C

With dmap; lithium hydroxide; triethylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;
DOI:10.1016/j.tet.2006.06.114