(4R,5R)-5-fluoro-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamido)hexanoic acid

Base Information

• Chemical Name: (4R,5R)-5-fluoro-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamido)hexanoic acid
• CAS No.: 1422255-67-1
• Molecular Formula: C₁₆H₁₉F₄NO₄
• Molecular Weight: 365.325
• Mol file: 1422255-67-1.mol

Synonyms:(4R,5R)-5-fluoro-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamido)hexanoic acid

Chemical Property of (4R,5R)-5-fluoro-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamido)hexanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R)-5-fluoro-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamido)hexanoic acid

There total 7 articles about (4R,5R)-5-fluoro-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamido)hexanoic acid 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:

(4R,5R)-4-ammonio-5-fluorohexanoate (1422255-55-7) + (R)-methoxytrifluoromethylphenylacetyl chloride (20445-33-4,39637-99-5) → (4S,5S)-5-fluoro-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamido)hexanoic acid (1422255-66-0) + (4R,5R)-5-fluoro-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamido)hexanoic acid (1422255-67-1)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; at 20 ℃;

DOI:10.1016/j.bmc.2012.12.009

Reference yield:

(4R,5R)-benzyl 4-azido-5-fluorohexanoate (1422255-62-6) → (4S,5S)-5-fluoro-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamido)hexanoic acid (1422255-66-0) + (4R,5R)-5-fluoro-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamido)hexanoic acid (1422255-67-1)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen / d(4)-methanol / 24 h / 20 °C

2: sodium hydrogencarbonate / water; acetone / 20 °C

With palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; In d⁽⁴⁾-methanol; water; acetone;

DOI:10.1016/j.bmc.2012.12.009

Reference yield:

Ethyl 4-hexenoate (34495-74-4) → (4S,5S)-5-fluoro-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamido)hexanoic acid (1422255-66-0) + (4R,5R)-5-fluoro-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamido)hexanoic acid (1422255-67-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: methanesulfonamide; AD-mix α / tert-butyl alcohol; water / 96 h / 4 °C

2.1: diethylamino-sulfur trifluoride / dichloromethane / 16 h / 0 - 20 °C

3.1: N,N-dimethyl-formamide / 16 h

4.1: di-isopropyl azodicarboxylate; triphenylphosphine; diphenyl phosphoryl azide / tetrahydrofuran / 0.25 h / 10 °C

4.2: -15 - 20 °C

5.1: palladium 10% on activated carbon; hydrogen / d(4)-methanol / 24 h / 20 °C

6.1: sodium hydrogencarbonate / water; acetone / 20 °C

With methanesulfonamide; diethylamino-sulfur trifluoride; AD-mix α; di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; triphenylphosphine; In tetrahydrofuran; dichloromethane; d⁽⁴⁾-methanol; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

DOI:10.1016/j.bmc.2012.12.009

upstream raw materials:

Ethyl 4-hexenoate

(S)-5-((S)-1-hydroxyethyl)dihydrofuran-2(3H)-one

(S)-5-((R)-1-fluoroethyl)dihydrofuran-2(3H)-one

(4R,5R)-4-ammonio-5-fluorohexanoate