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

Base Information

• Chemical Name: (2'S,4'R)-(-)-5-chloro-3-ethyl-N-<(1-ethyl-4-methanesulfonyloxy-2-pyrrolidinyl)methyl>-6-methoxysalicylamide
• CAS No.: 140161-20-2
• Molecular Formula: C₁₈H₂₇ClN₂O₆S
• Molecular Weight: 434.941
• Mol file: 140161-20-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (2'S,4'R)-(-)-5-chloro-3-ethyl-N-<(1-ethyl-4-methanesulfonyloxy-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: 84.0%

methanesulfonyl chloride (124-63-0) + (2'S,4'R)-(-)-5-chloro-3-ethyl-N-<(1-ethyl-4-hydroxy-2-pyrrolidinyl)methyl>-6-methoxysalicylamide (140161-18-8) → (2'S,4'R)-(-)-5-chloro-3-ethyl-N-<(1-ethyl-4-methanesulfonyloxy-2-pyrrolidinyl)methyl>-6-methoxysalicylamide (140161-20-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1248/cpb.39.3211

Reference yield:

trans-4-hydroxy-L-proline ethyl ester hydrochloride (33996-30-4) → (2'S,4'R)-(-)-5-chloro-3-ethyl-N-<(1-ethyl-4-methanesulfonyloxy-2-pyrrolidinyl)methyl>-6-methoxysalicylamide (140161-20-2)

Guidance literature:

Multi-step reaction with 7 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

7: 84 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

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; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1248/cpb.39.3211

Reference yield:

3-chloro-5-ethyl-6-hydroxy-2-methoxybenzoic acid (101536-78-1) → (2'S,4'R)-(-)-5-chloro-3-ethyl-N-<(1-ethyl-4-methanesulfonyloxy-2-pyrrolidinyl)methyl>-6-methoxysalicylamide (140161-20-2)

Guidance literature:

Multi-step reaction with 3 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

3: 84 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

With tetrabutyl ammonium fluoride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1248/cpb.39.3211

upstream raw materials:

methanesulfonyl chloride

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

trans-4-hydroxy-L-proline ethyl ester hydrochloride

3-chloro-5-ethyl-6-hydroxy-2-methoxybenzoic acid

Downstream raw materials:

fluoroeticlopride