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

Base Information

Chemical Name:(4S,5R)-5-fluoro-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamido)hexanoic acid
CAS No.:1422255-68-2
Molecular Formula:C₁₆H₁₉F₄NO₄
Molecular Weight:365.325
Hs Code.:

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

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

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

There total 8 articles about (4S,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: 91.0%

: 1422255-56-8
(4S,5R)-4-ammonio-5-fluorohexanoate

: 20445-33-4,39637-99-5
(R)-methoxytrifluoromethylphenylacetyl chloride

: 1422255-68-2
(4S,5R)-5-fluoro-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamido)hexanoic acid

Guidance literature:: With sodium hydrogencarbonate; In water; acetone; at 20 ℃;
DOI:10.1016/j.bmc.2012.12.009

Reference yield:

: 54656-51-8
(R)-5-((S)-1-hydroxyethyl)dihydrofuran-2(3H)-one

: 1422255-68-2
(4S,5R)-5-fluoro-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamido)hexanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate / dichloromethane / 24.5 h / -78 - 20 °C

2.1: potassium hydroxide; methanol / 16 h / 20 °C

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

4.1: di-isopropyl azodicarboxylate; triphenylphosphine; N-ethyl-N,N-diisopropylamine / 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 methanol; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate; potassium hydroxide; In tetrahydrofuran; dichloromethane; d⁽⁴⁾-methanol; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.bmc.2012.12.009

Reference yield:

: 34495-74-4
Ethyl 4-hexenoate

: 1422255-68-2
(4S,5R)-5-fluoro-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamido)hexanoic acid

Guidance literature:: Multi-step reaction with 9 steps

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

2.1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 0 - 20 °C / Inert atmosphere

3.1: potassium hydroxide / ethanol / 2 h / 60 °C

3.2: 24 h / 20 °C

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate / dichloromethane / 24.5 h / -78 - 20 °C

5.1: potassium hydroxide; methanol / 16 h / 20 °C

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

7.1: di-isopropyl azodicarboxylate; triphenylphosphine; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h / 10 °C

7.2: -15 - 20 °C

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

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

With methanol; methanesulfonamide; di-isopropyl azodicarboxylate; AD-mix β; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate; potassium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; d⁽⁴⁾-methanol; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 2.1: |Mitsunobu Displacement;
DOI:10.1016/j.bmc.2012.12.009