1-[(2R)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: 1-[(2R)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]pyrrolidine-2-carboxylic acid
• CAS No.: 7669-64-9
• Molecular Formula: C₂₂H₂₄N₂O₅
• Molecular Weight: 396.443
• European Community (EC) Number: 231-645-8
• Mol file: 7669-64-9.mol

Synonyms:7669-64-9

Chemical Property of 1-[(2R)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]pyrrolidine-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 107-108 °C
• Boiling Point: 669.586°C at 760 mmHg
• PKA: 3.51±0.20(Predicted)
• Flash Point: 358.753°C
• PSA: 95.94000
• Density: 1.292g/cm³
• LogP: 2.92850
• Storage Temp.: -15°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 396.16852187
• Heavy Atom Count: 29
• Complexity: 570

Purity/Quality:

99% ^*data from raw suppliers

Z-PHE-PRO-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)C(CC2=CC=CC=C2)NC(=O)OCC3=CC=CC=C3)C(=O)O
• Isomeric SMILES: C1CC(N(C1)C(=O)[C@@H](CC2=CC=CC=C2)NC(=O)OCC3=CC=CC=C3)C(=O)O

Technology Process of 1-[(2R)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]pyrrolidine-2-carboxylic acid

There total 23 articles about 1-[(2R)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]pyrrolidine-2-carboxylic 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: 95.0%

L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) + (S)-benzyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate (769922-77-2) → (2S)-1-((2S)-2-[[(benzyloxy)carbonyl]amino]-3-phenylpropanoyl)tetrahydro-1H-pyrrole-2-carboxylic acid (7669-64-9,17460-56-9,17460-57-0)

Guidance literature:

With triethylamine; In water; acetonitrile; at 50 ℃; for 0.166667h; Microwave irradiation;

DOI:10.1002/chem.201103143

Reference yield: 79.12%

N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester (2578-84-9) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (2S)-1-((2S)-2-[[(benzyloxy)carbonyl]amino]-3-phenylpropanoyl)tetrahydro-1H-pyrrole-2-carboxylic acid (7669-64-9,17460-56-9,17460-57-0)

Guidance literature:

With sodium hydroxide; In N,N-dimethyl-formamide; at 20 ℃;

Reference yield: 79.0%

(S)-benzyloxycarbonylphenylalanine pentafluorophenyl ester (17543-49-6) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (2S)-1-((2S)-2-[[(benzyloxy)carbonyl]amino]-3-phenylpropanoyl)tetrahydro-1H-pyrrole-2-carboxylic acid (7669-64-9,17460-56-9,17460-57-0)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; for 0.00833333h; microwave irradiation;

upstream raw materials:

methyl ((benzyloxy)carbonyl)-L-phenylalanyl-L-prolinate

N-(benzyloxycarbonyl)-phenylalanine-N-hydroxysuccinimide ester

L-proline

N-Cbz-L-Phe

Downstream raw materials:

Z-Phe-Pro-Gly-EtDa<*>Gly<*>Gly-Boc

C₂₇H₃₂N₂O₇

(2S,3S)-2-{[(S)-1-((S)-2-Amino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-hydroxy-butyric acid methyl ester

(5S,8S,11R,14S,17R,20S,22aS)-5,11-Dibenzyl-20-((S)-1-hydroxy-ethyl)-8,14-bis-hydroxymethyl-17-isopropyl-hexadecahydro-3a,6,9,12,15,18,21-heptaaza-cyclopentacyclohenicosene-4,7,10,13,16,19,22-heptaone

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