(S)-N-Z-3-AMINO 3-PHENYLPROPIONIC ACID

Base Information

• Chemical Name: (S)-N-Z-3-AMINO 3-PHENYLPROPIONIC ACID
• CAS No.: 14441-08-8
• Molecular Formula: C17H17 N O4
• Molecular Weight: 299.326
• Hs Code.: 2924299090
• Mol file: 14441-08-8.mol

Synonyms:Benzenepropanoicacid, b-[[(phenylmethoxy)carbonyl]amino]-,(S)-; Hydrocinnamic acid, b-(carboxyamino)-, N-benzyl ester, (-)- (8CI)

Chemical Property of (S)-N-Z-3-AMINO 3-PHENYLPROPIONIC ACID

Chemical Property:

• Melting Point: 121.5-122.5 °C
• Boiling Point: 507.9±50.0 °C(Predicted)
• PKA: 4.31±0.10(Predicted)
• PSA: 79.12000
• Density: 1.246±0.06 g/cm3(Predicted)
• LogP: 3.33320

Purity/Quality:

97% ^*data from raw suppliers

(S)-Cbz-beta3-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-N-Z-3-AMINO 3-PHENYLPROPIONIC ACID

There total 21 articles about (S)-N-Z-3-AMINO 3-PHENYLPROPIONIC 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%

tert-butyl (3S)-N-(benzyloxycarbonyl)-3-amino-3-phenylpropanoate (245323-41-5) → (3S)-N-(benzyloxycarbonyl)-3-amino-3-phenylpropanoic acid (14441-08-8)

Guidance literature:

With dimethylsulfide; In dichloromethane; trifluoroacetic acid; at 20 ℃; for 3h;

DOI:10.1021/jo990756k

Reference yield: 90.3%

methyl (S)-β-[[(phenylmethoxy)carbonyl]amino]-benzenepropanoate (32975-59-0) → (3S)-N-(benzyloxycarbonyl)-3-amino-3-phenylpropanoic acid (14441-08-8)

Guidance literature:

With sodium hydroxide; In methanol; isopropyl alcohol; at 20 ℃; for 2h; Inert atmosphere; Large scale;

DOI:10.1021/op8000614

Reference yield: 84.0%

(R)-(-)-α-benzyloxycarbonylaminobenzyldiazomethyl ketone (32975-58-9) → (3S)-N-(benzyloxycarbonyl)-3-amino-3-phenylpropanoic acid (14441-08-8)

Guidance literature:

With silver benzoate; In 1,4-dioxane; water; for 0.0166667h; microwave irradiation;

upstream raw materials:

(S)-3-amino-3-phenylpropanoic acid

benzyl chloroformate

(S)-(-)-β-Phenyl-β-alanine hydrochloride

tert-butyl (3S)-N-(benzyloxycarbonyl)-3-amino-3-phenylpropanoate

Downstream raw materials:

(S)-benzyl [5-(1,3-dioxoisoindolin-2-yl)-3-oxo-1-phenylpentyl]carbamate

(S)-benzyl [2-(2-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-1,3-dioxan-2-yl)-1-phenylethyl]carbamate

(S)-benzyl [2-(2-(2-aminoethyl)-1,3-dioxan-2-yl)-1-phenylethyl]carbamate

(S)-benzyl [1-phenyl-2-(2-(2-(2,2,2-trifluoroacetamido)ethyl)-1,3-dioxan-2-yl)ethyl]carbamate

Refernces

• 1、 Abrunhosa-Thomas, Isabelle,Plas, Aurelie,Kandepedu, Nishanth,Chalard, Pierre,Troin, Yves. "Efficient synthesis of β'-amino-α, β-unsaturated ketones". . p. 486 - 495. Retrieved 2013/04/23.
• 2、 Haycock-Lewandowski, Sarah J.,Wilder, Alexander,Ahman, Jens. "Development of a bulk enabling route to maraviroc (UK-427,857), a CCR-5 receptor antagonist". . p. 1094 - 1103. Retrieved 2013/01/03.