H-PHE-PYRROLIDIDE

Base Information

• Chemical Name: H-PHE-PYRROLIDIDE
• CAS No.: 56414-89-2
• Molecular Formula: C13H18N2O
• Molecular Weight: 218.299
• Mol file: 56414-89-2.mol

Synonyms:Pyrrolidine,1-(2-amino-1-oxo-3-phenylpropyl)-, (S)-;Pyrrolidine,1-[(2S)-2-amino-1-oxo-3-phenylpropyl]- (9CI);(2S)-1-oxo-3-phenyl-1-pyrrolidin-1-ylpropan-2-amine;

Chemical Property of H-PHE-PYRROLIDIDE

Chemical Property:

• Vapor Pressure: 1.59E-06mmHg at 25°C
• Refractive Index: 1.578
• Boiling Point: 397.4 °C at 760 mmHg
• PKA: 7.90±0.33(Predicted)
• Flash Point: 194.1 °C
• PSA: 46.33000
• Density: 1.135 g/cm³
• LogP: 1.81700
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

1-[(2S)-2-Amino-1-oxo-3-phenylpropyl]pyrrolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of H-PHE-PYRROLIDIDE

There total 4 articles about H-PHE-PYRROLIDIDE 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:

Nα-(tert-butoxycarbonyl)-L-phenylalanine-N-pyrrolidinamide (125139-05-1) → L-phenylalanine N1,N1-(tetramethylene)amide (56414-89-2)

Guidance literature:

With methanol; acetyl chloride; at 0 - 20 ℃; for 4h;

DOI:10.1021/ja053368a

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → L-phenylalanine N1,N1-(tetramethylene)amide (56414-89-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / Et₃N; (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium*PF₆ / tetrahydrofuran / 8 h / 0 - 20 °C

2: AcCl; MeOH / 4 h / 0 - 20 °C

With methanol; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; acetyl chloride; In tetrahydrofuran;

DOI:10.1021/ja053368a

Reference yield:

pyrrolidine (123-75-1) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → D-phenylalanine pyrrolidineamide + L-phenylalanine N1,N1-(tetramethylene)amide (56414-89-2)

Guidance literature:

With tris(2,2,2-trifluoroethyl) borate; at 125 ℃; for 15h; Overall yield = 48 %; Overall yield = 105 mg; chemoselective reaction; Green chemistry;

DOI:10.1002/chem.201800372

upstream raw materials:

pyrrolidine

N-tert-butoxycarbonyl-L-phenylalanine

N^α-(tert-butoxycarbonyl)-L-phenylalanine-N-pyrrolidinamide

L-phenylalanine

Downstream raw materials:

C₄₈H₆₇N₅O₆

(+)-(S)-2-amino-1-phenyl-3-(pyrrolidin-1-yl)propane

(S)-octanedioic acid (1-benzyl-2-oxo-2-pyrrolidin-1-yl-ethyl)amide trityloxy-amide

N²<(R)-2-benzamido-1,2,3,4-tetrahydro-7-methoxynaphthalene-2-carbonyl>-L-phenylalanine N¹,N¹-(tetramethylene)amide

Refernces

• 1、 Hu, Shenshen,Zhang, Long,Li, Jiuyuan,Luo, Sanzhong,Cheng, Jin-Pei. "Chiral primary amine catalyzed asymmetric direct cross-aldol reaction of acetaldehyde". experimental part. p. 3347 - 3352. Retrieved 2011/08/03.
• 2、 Nagamine, Takashi,Inomata, Kohei,Endo, Yasuyuki. "A new chiral synthesis of a bicyclic enedione containing a seven-membered ring mediated by a combination of chiral amine and Bronsted acid". experimental part. p. 1191 - 1204. Retrieved 2009/06/28.