methyl (3R)-3-amino-3-phenylpropanoate

Base Information

• Chemical Name: methyl (3R)-3-amino-3-phenylpropanoate
• CAS No.: 37088-67-8
• Molecular Formula: C10H13 N O2
• Molecular Weight: 179.219
• Hs Code.: 2922498590
• DSSTox Substance ID: DTXSID80354972
• Nikkaji Number: J694.647J
• Wikidata: Q72487280
• Mol file: 37088-67-8.mol

Synonyms:methyl (3R)-3-amino-3-phenylpropanoate;37088-67-8;(R)-METHYL 3-AMINO-3-PHENYLPROPANOATE;(R)-3-Amino-3-phenyl propionic acid methylester;SCHEMBL1144412;DTXSID80354972;XKIOBYHZFPTKCZ-SECBINFHSA-N;MFCD08056712;AKOS027439496;methyl (r)-3-amino-3-phenylpropionate;Methyl (R)-3-amino-3-phenylpropanoate;BS-28001;CS-0208141;(R)-METHYL3-AMINO-3-PHENYLPROPANOATE;EN300-66422;N12271;(R)-3-Amino-3-phenyl-propionic acid methyl ester;A898291

Chemical Property of methyl (3R)-3-amino-3-phenylpropanoate

Chemical Property:

• Vapor Pressure: 0.00324mmHg at 25°C
• Refractive Index: 1.529
• Boiling Point: 283°C at 760 mmHg
• Flash Point: 141.7°C
• PSA: 52.32000
• Density: 1.098g/cm³
• LogP: 1.94980
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 164

Purity/Quality:

99% ^*data from raw suppliers

Benzenepropanoicacid,?-amino-,methylester,(?R)- 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CC(C1=CC=CC=C1)N
• Isomeric SMILES: COC(=O)C[C@H](C1=CC=CC=C1)N
• Uses: Used in the stereoselective synthesis of phenylalanine esters drugs.

Technology Process of methyl (3R)-3-amino-3-phenylpropanoate

There total 51 articles about methyl (3R)-3-amino-3-phenylpropanoate 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%

methanol (67-56-1) + (R)-3-phenyl-3-aminopropionic acid (614-19-7,3646-50-2,13921-90-9,40856-44-8) → methyl (3R)-3-amino-3-phenylpropanoate (37088-67-8)

Guidance literature:

With sulfuric acid; at 0 - 20 ℃;

DOI:10.1002/adsc.202100719

Reference yield: 98.0%

(R)-N-benzyl-β-phenylalanine methyl ester → methyl (3R)-3-amino-3-phenylpropanoate (37088-67-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1039/c0ob00570c

Reference yield: 92.0%

(SS,3R)-(+)-methyl 3-[N-(p-toluenesulfinyl)amino]-3-(phenyl)propanoate (158009-86-0) → methyl (3R)-3-amino-3-phenylpropanoate (37088-67-8)

Guidance literature:

With trifluoroacetic acid; In methanol;

DOI:10.1016/S0040-4039(00)76775-X

upstream raw materials:

(S_S,3R)-(+)-methyl 3-[N-(p-toluenesulfinyl)amino]-3-(phenyl)propanoate

(R)-3-tert-butoxycarbonylamino-3-phenylpropionic acid methyl ester

(-)-menthol

methanol

Downstream raw materials:

methyl (3R)-3-(2,4-dinitroanilino)-3-phenylpropanoate

C₁₄H₁₇NO₅

(R)-3-phenyl-3-aminopropionic acid

(3R)-4-phenyl-2-azetidinone

Refernces

• 1、 Ye, Jianheng,Wang, Chao,Chen, Lin,Wu, Xinjun,Zhou, Li,Sun, Jian. "Chiral Lewis Base-Catalyzed, Enantioselective Reduction of Unprotected β-Enamino Esters with Trichlorosilane". supporting information. p. 1042 - 1047. Retrieved 2016/04/19.
• 2、 Sundell, Riku,Kanerva, Liisa T.. "Studies on N-activation for the lipase-catalyzed enantioselective preparation of β-amino esters from 4-phenylazetidin-2-one". . p. 1500 - 1506. Retrieved 2015/03/04.