(2S,3S)-3-Amino-2-Hydroxy-4-Phenylbutyric Acid Hydrochloride

Base Information

• Chemical Name: (2S,3S)-3-Amino-2-Hydroxy-4-Phenylbutyric Acid Hydrochloride
• CAS No.: 129593-20-0
• Molecular Formula: C₁₀H₁₃NO₃*ClH
• Molecular Weight: 231.679
• Mol file: 129593-20-0.mol

Synonyms:Benzenebutanoicacid, b-amino-a-hydroxy-, hydrochloride, (aS,bS)- (9CI); Benzenebutanoic acid, b-amino-a-hydroxy-, hydrochloride,[S-(R*,R*)]-; (2S,3S)-3-Amino-2-hydroxy-4-phenylbutyric acid hydrochloride

Chemical Property of (2S,3S)-3-Amino-2-Hydroxy-4-Phenylbutyric Acid Hydrochloride

Chemical Property:

• Melting Point: 228-230 °C (decomp)
• PSA: 83.55000
• LogP: 1.50420

Purity/Quality:

97% ^*data from raw suppliers

(2S,3S)-3-AMINO-2-HYDROXY-4-PHENYLBUTYRIC ACID HYDROCHLORIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,3S)-3-Amino-2-Hydroxy-4-Phenylbutyric Acid Hydrochloride

There total 11 articles about (2S,3S)-3-Amino-2-Hydroxy-4-Phenylbutyric Acid Hydrochloride 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: 100.0%

(3-R)-2-acetoxy-3-isopropoxycarbonylamino-4-phenylbutyronitrile (129867-99-8,129868-00-4) → 3-amino-2-hydroxy-4-phenylbutyric acid hydrochloride (119642-28-3,128223-55-2,128223-56-3,129593-20-0,129618-41-3)

Guidance literature:

With hydrogenchloride; In ethyl acetate; at 80 - 100 ℃; for 14h;

DOI:10.1246/bcsj.65.360

Reference yield:

tert-butyl (2R)-1-cyano-1-hydroxy-3-phenylpropan-2-yl carbamate → 3-amino-2-hydroxy-4-phenylbutyric acid hydrochloride (119642-28-3,128223-55-2,128223-56-3,129593-20-0,129618-41-3)

Guidance literature:

With hydrogenchloride; methoxybenzene; In 1,4-dioxane; water; for 4.5h; Reflux;

DOI:10.1055/s-0031-1289586

Reference yield:

D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) → 3-amino-2-hydroxy-4-phenylbutyric acid hydrochloride (119642-28-3,128223-55-2,128223-56-3,129593-20-0,129618-41-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / SOCl₂

2: 89 percent / tetrahydrofuran / 1 h / 0 °C

3: 98 percent / LiCl, NaBH₄ / ethanol / 17 h / Ambient temperature

4: 81 percent / SO₃*Py, Et₃N / toluene; dimethylsulfoxide / 0.33 h / Ambient temperature

5: 100 percent / benzyltributylammonium chloride / CH₂Cl₂; H₂O / 3 h / 0 °C

6: 100 percent / aq. HCl / ethyl acetate / 14 h / 80 - 100 °C

With hydrogenchloride; sodium tetrahydroborate; thionyl chloride; pyridine-SO₃ complex; benzyltri(n-butyl)ammonium chloride; triethylamine; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene;

DOI:10.1246/bcsj.65.360

upstream raw materials:

(3-R)-2-acetoxy-3-isopropoxycarbonylamino-4-phenylbutyronitrile

D-(R)-phenylalanine

D-phenylalanine methyl ester hydrochloride

(R)-N-(isopropoxycarbonyl)phenylalaninal

Downstream raw materials:

(R)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-hydroxy-4-phenylbutanoic acid

methyl (2R,3R)-2-acetoxy-3-acetylamino-4-phenylbutyrate

methyl (2S,3R)-2-acetoxy-3-acetylamino-4-phenylbutyrate

Refernces

• 1、 Johnson, Erik P.,Hubieki, M. Patricia,Combs, Andrew P.,Teleha, Christopher A.. "Preparation of α-hydroxy-β-Fmoc amino acids from N-Boc amino acids". experimental part. p. 4023 - 4026. Retrieved 2012/01/12.