L-Proline, 1-[4-(1,1-dimethylethyl)-3-methoxybenzoyl]-4-(ethoxymethyl)-2-(2-methyl propyl)-5-(2-thiazolyl)-, 1,1-dimethylethyl ester, (4S,5R)-

Base Information

Chemical Name:L-Proline, 1-[4-(1,1-dimethylethyl)-3-methoxybenzoyl]-4-(ethoxymethyl)-2-(2-methyl propyl)-5-(2-thiazolyl)-, 1,1-dimethylethyl ester, (4S,5R)-
CAS No.:687636-16-4
Molecular Formula:C31H46N2O5S
Molecular Weight:558.783
Hs Code.:

L-Proline,
1-[4-(1,1-dimethylethyl)-3-methoxybenzoyl]-4-(ethoxymethyl)-2-(2-methyl
propyl)-5-(2-thiazolyl)-, 1,1-dimethylethyl ester, (4S,5R)-

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Chemical Property of L-Proline, 1-[4-(1,1-dimethylethyl)-3-methoxybenzoyl]-4-(ethoxymethyl)-2-(2-methyl propyl)-5-(2-thiazolyl)-, 1,1-dimethylethyl ester, (4S,5R)-

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Technology Process of L-Proline, 1-[4-(1,1-dimethylethyl)-3-methoxybenzoyl]-4-(ethoxymethyl)-2-(2-methyl propyl)-5-(2-thiazolyl)-, 1,1-dimethylethyl ester, (4S,5R)-

There total 7 articles about L-Proline, 1-[4-(1,1-dimethylethyl)-3-methoxybenzoyl]-4-(ethoxymethyl)-2-(2-methyl propyl)-5-(2-thiazolyl)-, 1,1-dimethylethyl ester, (4S,5R)- 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: 57.0%

: 687636-14-2
1,1-dimethylethyl (4S,5R)-1-{[4-(1,1-dimethylethyl)-3-(methyloxy)phenyl]carbonyl}-4-(hydroxymethyl)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)-L-prolinate

: 75-03-6
ethyl iodide

: 687636-16-4
(2S,4S,5R)-2-isobutyl-1-(3-methoxy-4-tert-butylbenzoyl)-4-ethoxymethyl-5-(1,3-thiazol-2-yl)-pyrrolidine-2-carboxylic acid 2-tert-butyl ester

Guidance literature:: 1,1-dimethylethyl (4S,5R)-1-{[4-(1,1-dimethylethyl)-3-(methyloxy)phenyl]carbonyl}-4-(hydroxymethyl)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)-L-prolinate; With sodium hydride; In N,N-dimethyl-formamide; at -15 ℃; for 0.166667h;

ethyl iodide; In N,N-dimethyl-formamide; at -15 - 10 ℃; for 24h;
DOI:10.1021/jm061207r

Reference yield:

: 75-03-6
ethyl iodide

: 687636-16-4
(2S,4S,5R)-2-isobutyl-1-(3-methoxy-4-tert-butylbenzoyl)-4-ethoxymethyl-5-(1,3-thiazol-2-yl)-pyrrolidine-2-carboxylic acid 2-tert-butyl ester

Guidance literature:: 1,1-dimethylethyl (4S,5R)-1-{[4-(1,1-dimethylethyl)-3-(methyloxy)phenyl]carbonyl}-4-(hydroxymethyl)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)-L-prolinate; With sodium hydride; In DMF (N,N-dimethyl-formamide); at -15 ℃; for 0.333333h;

ethyl iodide; In DMF (N,N-dimethyl-formamide); at -15 - 10 ℃; for 24h;

Reference yield:

: 521955-41-9
2-[N-(1,3-thiazol-2-ylmethylene)amino]-4-methylpentanoic acid tert-butyl ester

: 687636-16-4
(2S,4S,5R)-2-isobutyl-1-(3-methoxy-4-tert-butylbenzoyl)-4-ethoxymethyl-5-(1,3-thiazol-2-yl)-pyrrolidine-2-carboxylic acid 2-tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: lithium bromide; triethylamine / tetrahydrofuran / 20 °C

2.1: (R)-(-)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate / propan-2-ol / 75 °C

3.1: 98 percent / triethylamine / CH₂Cl₂ / 19 h / 0 - 20 °C

4.1: 85 percent / LiAlH₄ / tetrahydrofuran / 5 h / -78 - -20 °C

5.1: sodium hydride / dimethylformamide / 0.17 h / -15 °C

5.2: 57 percent / dimethylformamide / 24 h / -15 - 10 °C

With lithium aluminium tetrahydride; (R)-1,1'-binaphthyl-2,2'-phosphoric acid; sodium hydride; triethylamine; lithium bromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/jm061207r