N-acetyl-D-proline

Base Information

• Chemical Name: N-acetyl-D-proline
• CAS No.: 59785-68-1
• Molecular Formula: C₇H₁₁NO₃
• Molecular Weight: 157.169
• Hs Code.: 2933990090
• European Community (EC) Number: 826-011-8
• DSSTox Substance ID: DTXSID00352112
• Nikkaji Number: J1.319.740G
• Wikidata: Q27120548
• Metabolomics Workbench ID: 56547
• ChEMBL ID: CHEMBL3137742
• Mol file: 59785-68-1.mol

Synonyms:N-acetyl-D-proline;59785-68-1;AC-D-PRO-OH;(2R)-1-acetylpyrrolidine-2-carboxylic acid;D-Proline, 1-acetyl-;(R)-1-Acetylpyrrolidine-2-carboxylic acid;1-ACETYL-D-PROLINE;CHEBI:44272;Acetyl-D-proline;4ayu;N-alpha-Actetyl-D-proline;Ac-D-Pro-OH, AldrichCPR;SCHEMBL428477;CHEMBL3137742;DTXSID00352112;GNMSLDIYJOSUSW-ZCFIWIBFSA-N;MFCD00080841;AKOS015841039;AM82194;CS-W017974;(R)-acetyl-pyrrolidine-2-carboxylic acid;DS-16114;(R,S)-1-Acetyl-pyrrolidine-2-carboxylic acid;EN300-211777;F10955;A832468;Q27120548;Z1078490036;N8P

Chemical Property of N-acetyl-D-proline

Chemical Property:

• Vapor Pressure: 2.31E-06mmHg at 25°C
• Refractive Index: 1.517
• Boiling Point: 366.2 °C at 760 mmHg
• PKA: 3.69±0.20(Predicted)
• Flash Point: 175.3 °C
• PSA: 57.61000
• Density: 1.274g/cm³
• LogP: 0.01980
• Storage Temp.: Store at RT.
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 157.07389321
• Heavy Atom Count: 11
• Complexity: 190

Purity/Quality:

99% ^*data from raw suppliers

Ac-D-Pro-OH ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)N1CCCC1C(=O)O
• Isomeric SMILES: CC(=O)N1CCC[C@@H]1C(=O)O

Technology Process of N-acetyl-D-proline

There total 2 articles about N-acetyl-D-proline 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: 78.0%

N-acetyl-L-proline benzyl ester (132090-10-9) → N-acetyl-L-proline (68-95-1,1074-79-9,59785-68-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 1h; under 760 Torr;

Reference yield:

L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → N-acetyl-L-proline (68-95-1,1074-79-9,59785-68-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) toluene-4-sulphonic acid monohydrate; 2.) Et₃N / 1.) benzene, reflux, aceotropic H₂O removal, 10 h; 2.) CH₂Cl₂, -5 deg C

2: 78 percent / H₂ / Pd/C (5 percent) / ethanol / 1 h / 760 Torr

With hydrogen; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In ethanol;

Reference yield:

N-acetyl-L-proline (68-95-1,1074-79-9,59785-68-1) → N-(N'-acetyl-L-prolyl)-L-phenylalanine (132090-09-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Et₃N, ethyl chloroformate / 1.) THF, -10 deg C, 30 min; 2.) -10 deg C to r.t.

2: 82 percent / H₂ / Pd/C (5 percent) / ethanol / 1 h / 760 Torr

With hydrogen; chloroformic acid ethyl ester; triethylamine; palladium on activated charcoal; In ethanol;

upstream raw materials:

N-acetyl-L-proline benzyl ester

L-proline

Downstream raw materials:

N-(N'-acetyl-L-prolyl)glycine benzyl ester

N-(N'-acetyl-L-prolyl)-L-alanine benzyl ester

N-(N'-acetyl-L-prolyl)-N-nitrosoglycine

N-(N'-acetyl-L-prolyl)-L-phenylalanine

Refernces