(2'S,4'R)-(-)-5-chloro-3-ethyl-N-<(1-ethyl-4-hydroxy-2-pyrrolidinyl)methyl>-6-methoxysalicylamide

Base Information

Chemical Name:(2'S,4'R)-(-)-5-chloro-3-ethyl-N-<(1-ethyl-4-hydroxy-2-pyrrolidinyl)methyl>-6-methoxysalicylamide
CAS No.:140161-18-8
Molecular Formula:C₁₇H₂₅ClN₂O₄
Molecular Weight:356.849
Hs Code.:

Synonyms:(2'S,4'R)-(-)-5-chloro-3-ethyl-N-<(1-ethyl-4-hydroxy-2-pyrrolidinyl)methyl>-6-methoxysalicylamide

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Chemical Property of (2'S,4'R)-(-)-5-chloro-3-ethyl-N-<(1-ethyl-4-hydroxy-2-pyrrolidinyl)methyl>-6-methoxysalicylamide

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Technology Process of (2'S,4'R)-(-)-5-chloro-3-ethyl-N-<(1-ethyl-4-hydroxy-2-pyrrolidinyl)methyl>-6-methoxysalicylamide

There total 8 articles about (2'S,4'R)-(-)-5-chloro-3-ethyl-N-<(1-ethyl-4-hydroxy-2-pyrrolidinyl)methyl>-6-methoxysalicylamide 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: 94.0%

: 140161-17-7
(2'S,4'R)-(-)-5-chloro-3-ethyl-N-<(1-ethyl-4-tert-butyldimethylsilyloxy-2-pyrrolidinyl)methyl>-6-methoxysalicylamide

: 140161-18-8
(2'S,4'R)-(-)-5-chloro-3-ethyl-N-<(1-ethyl-4-hydroxy-2-pyrrolidinyl)methyl>-6-methoxysalicylamide

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 72h; Ambient temperature;
DOI:10.1248/cpb.39.3211

Reference yield:

: 33996-30-4
trans-4-hydroxy-L-proline ethyl ester hydrochloride

: 140161-18-8
(2'S,4'R)-(-)-5-chloro-3-ethyl-N-<(1-ethyl-4-hydroxy-2-pyrrolidinyl)methyl>-6-methoxysalicylamide

Guidance literature:: Multi-step reaction with 6 steps

1: 54 percent / triethylamine / dioxane; H₂O / 120 h / Ambient temperature

2: 99 percent / imidazole / dimethylformamide / 72 h

3: 93 percent / KI, NH₃ / methanol / 168 h / 40 °C

4: 82 percent / LiAlH₄ / diethyl ether / 48 h / Heating

5: 1.) 1-hydroxybenzotriazole, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride / 1.) CH₂Cl₂, a) -10 deg C, 100 min, b) RT, 30 min, 2.) CH₂Cl₂, RT, overnight

6: 94 percent / n-Bu₄NF / tetrahydrofuran / 72 h / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; potassium iodide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; water; N,N-dimethyl-formamide;
DOI:10.1248/cpb.39.3211

Reference yield:

: 101536-78-1
3-chloro-5-ethyl-6-hydroxy-2-methoxybenzoic acid

: 140161-18-8
(2'S,4'R)-(-)-5-chloro-3-ethyl-N-<(1-ethyl-4-hydroxy-2-pyrrolidinyl)methyl>-6-methoxysalicylamide

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) 1-hydroxybenzotriazole, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride / 1.) CH₂Cl₂, a) -10 deg C, 100 min, b) RT, 30 min, 2.) CH₂Cl₂, RT, overnight

2: 94 percent / n-Bu₄NF / tetrahydrofuran / 72 h / Ambient temperature

With tetrabutyl ammonium fluoride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran;
DOI:10.1248/cpb.39.3211