(2R,3S,4S)-4-Acetyl-2-ethynyl-3-hydroxy-4-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid phenyl ester

Base Information

• Chemical Name: (2R,3S,4S)-4-Acetyl-2-ethynyl-3-hydroxy-4-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid phenyl ester
• CAS No.: 161824-76-6
• Molecular Formula: C₂₁H₁₉NO₄
• Molecular Weight: 349.386

Synonyms:(2R,3S,4S)-4-Acetyl-2-ethynyl-3-hydroxy-4-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid phenyl ester

Chemical Property of (2R,3S,4S)-4-Acetyl-2-ethynyl-3-hydroxy-4-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid phenyl ester

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Technology Process of (2R,3S,4S)-4-Acetyl-2-ethynyl-3-hydroxy-4-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid phenyl ester

There total 1 articles about (2R,3S,4S)-4-Acetyl-2-ethynyl-3-hydroxy-4-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid phenyl 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: 52.0%

(1aR,2R,7bS)-2-Ethynyl-7b-(1-hydroxy-1-methyl-ethyl)-1a,7b-dihydro-2H-1-oxa-3-aza-cyclopropa[a]naphthalene-3-carboxylic acid phenyl ester (161824-75-5) → (2R,3S,4S)-4-Acetyl-2-ethynyl-3-hydroxy-4-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid phenyl ester (161824-76-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃;

DOI:10.1016/0040-4039(94)80032-4

Reference yield:

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride (39637-99-5,20445-33-4) + (2R,3S,4S)-4-Acetyl-2-ethynyl-3-hydroxy-4-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid phenyl ester (161824-76-6) → (2R,3S,4S)-4-Acetyl-2-ethynyl-4-methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid phenyl ester

Guidance literature:

With dmap; triethylamine;

DOI:10.1016/0040-4039(94)80032-4

Reference yield:

(R)-methoxytrifluoromethylphenylacetyl chloride (20445-33-4,39637-99-5) + (2R,3S,4S)-4-Acetyl-2-ethynyl-3-hydroxy-4-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid phenyl ester (161824-76-6) → (2R,3S,4S)-4-Acetyl-2-ethynyl-4-methyl-3-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid phenyl ester

Guidance literature:

With dmap; triethylamine;

DOI:10.1016/0040-4039(94)80032-4

upstream raw materials:

(1aR,2R,7bS)-2-Ethynyl-7b-(1-hydroxy-1-methyl-ethyl)-1a,7b-dihydro-2H-1-oxa-3-aza-cyclopropa[a]naphthalene-3-carboxylic acid phenyl ester

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