4-amino-5-fluoro-3-phenylpentanoic acid

Base Information

• Chemical Name: 4-amino-5-fluoro-3-phenylpentanoic acid
• CAS No.: 124687-35-0
• Molecular Formula: C₁₁H₁₄FNO₂*ClH
• Molecular Weight: 247.697
• Mol file: 124687-35-0.mol

Synonyms:Benzenepropanoicacid, b-(1-amino-2-fluoroethyl)-,hydrochloride, (R*,R*)- (9CI); Benzenepropanoic acid, b-(1-amino-2-fluoroethyl)-,hydrochloride, (R*,R*)-(?à)-

Chemical Property of 4-amino-5-fluoro-3-phenylpentanoic acid

Chemical Property:

• Vapor Pressure: 6.3E-06mmHg at 25°C
• Boiling Point: 363.7°C at 760 mmHg
• Flash Point: 173.8°C
• PSA: 63.32000
• LogP: 3.04400

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-amino-5-fluoro-3-phenylpentanoic acid

There total 6 articles about 4-amino-5-fluoro-3-phenylpentanoic 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:

ethyl 3-phenyl-2-propenoate (103-36-6) → (3S,4S),(3R,4R)-4-amino-5-fluoro-3-phenylpentanoic acid hydrochloride (124687-35-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) NaOEt / 1.) EtOH, RT, 30 min, 2.) a) RT, 2 h, b) reflux, 14 h

2: 90 percent / aq. KOH / ethanol / 10 h / Ambient temperature

3: 0.1 h / 180 °C

4: 89 percent / LiBH₄ / tetrahydrofuran / 28 h / Ambient temperature

5: 84 percent / polymer-bound triphenylphosphine, CBr₄ / acetonitrile / 45 h / Heating

6: AgF / acetonitrile / 40 h / Ambient temperature

7: 6 N HCl / 9.5 h / Heating

With hydrogenchloride; potassium hydroxide; lithium borohydride; carbon tetrabromide; polymer-bound triphenylphosphine; sodium ethanolate; silver fluoride; In tetrahydrofuran; ethanol; acetonitrile;

DOI:10.1021/jm00165a008

Reference yield:

(+/-)-cis-5-carbethoxy-trans-5-carboxy-4-phenyl-2-pyrrolidinone (124687-28-1) → (3S,4S),(3R,4R)-4-amino-5-fluoro-3-phenylpentanoic acid hydrochloride (124687-35-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 0.1 h / 180 °C

2: 89 percent / LiBH₄ / tetrahydrofuran / 28 h / Ambient temperature

3: 84 percent / polymer-bound triphenylphosphine, CBr₄ / acetonitrile / 45 h / Heating

4: AgF / acetonitrile / 40 h / Ambient temperature

5: 6 N HCl / 9.5 h / Heating

With hydrogenchloride; lithium borohydride; carbon tetrabromide; polymer-bound triphenylphosphine; silver fluoride; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jm00165a008

Reference yield:

(+/-)-cis-5-(hydroxymethyl)-4-phenyl-2-pyrrolidinone (124687-29-2) → (3S,4S),(3R,4R)-4-amino-5-fluoro-3-phenylpentanoic acid hydrochloride (124687-35-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / polymer-bound triphenylphosphine, CBr₄ / acetonitrile / 45 h / Heating

2: AgF / acetonitrile / 40 h / Ambient temperature

3: 6 N HCl / 9.5 h / Heating

With hydrogenchloride; carbon tetrabromide; polymer-bound triphenylphosphine; silver fluoride; In acetonitrile;

DOI:10.1021/jm00165a008

upstream raw materials:

(+/-)-cis-5-(fluoromethyl)-4-phenyl-2-pyrrolidinone

ethyl 3-phenyl-2-propenoate

(+/-)-cis-5-carbethoxy-trans-5-carboxy-4-phenyl-2-pyrrolidinone

(+/-)-cis-5-(hydroxymethyl)-4-phenyl-2-pyrrolidinone

Refernces