benzyl (2R)-2-carbamoylpyrrolidine-1-carboxylate

Base Information

• Chemical Name: benzyl (2R)-2-carbamoylpyrrolidine-1-carboxylate
• CAS No.: 62937-47-7
• Molecular Formula: C13H16N2O3
• Molecular Weight: 248.282
• Hs Code.: 2933990090
• European Community (EC) Number: 624-701-1
• DSSTox Substance ID: DTXSID90426215
• Wikidata: Q76393629
• Mol file: 62937-47-7.mol

Synonyms:62937-47-7;(R)-2-Carbamoyl-1-N-Cbz-pyrrolidine;Z-D-PRO-NH2;(R)-2-carbamoyl-n-cbz-pyrrolidine;benzyl (2R)-2-carbamoylpyrrolidine-1-carboxylate;(R)-BENZYL 2-CARBAMOYLPYRROLIDINE-1-CARBOXYLATE;Z-L-Prolinamide;(R)-2-Carbamoyl-1-Cbz-pyrrolidine;Cbz-D-prolinamide;SCHEMBL1437568;DTXSID90426215;ZCGHEBMEQXMRQL-LLVKDONJSA-N;AB3071;MFCD00237361;N-alpha-Carbobenzoxy-D-proline amide;AKOS016843462;AS-15066;Benzyl (R)-2-carbamoylpyrrolidine-1-carboxylate;A834103;1-Pyrrolidinecarboxylicacid,2-(aminocarbonyl)-,phenylmethyl ester,(2R)-

Chemical Property of benzyl (2R)-2-carbamoylpyrrolidine-1-carboxylate

Chemical Property:

• Vapor Pressure: 7.61E-09mmHg at 25°C
• Melting Point: 90-95 °C
• Refractive Index: 1.581
• Boiling Point: 465.6 °C at 760 mmHg
• PKA: 15.95±0.20(Predicted)
• Flash Point: 235.4 °C
• PSA: 72.63000
• Density: 1.263 g/cm³
• LogP: 1.91110
• Storage Temp.: Store at RT.
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 248.11609238
• Heavy Atom Count: 18
• Complexity: 313

Purity/Quality:

98%,99%, ^*data from raw suppliers

Z-D-proline amide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)OCC2=CC=CC=C2)C(=O)N
• Isomeric SMILES: C1C[C@@H](N(C1)C(=O)OCC2=CC=CC=C2)C(=O)N

Technology Process of benzyl (2R)-2-carbamoylpyrrolidine-1-carboxylate

There total 7 articles about benzyl (2R)-2-carbamoylpyrrolidine-1-carboxylate 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: 83.0%

N-carbobenzoxy-(R)-proline-p-nitrophenol ester (15246-82-9) → (2R)-2-carbamoyl-pyrrolidine-1-carboxylic acid benzyl ester (62937-47-7,58274-22-9)

Guidance literature:

With ammonia; triethylamine; In methanol; at 0 ℃; Reflux;

DOI:10.1016/j.ejmech.2008.12.022

Reference yield: 79.0%

Z-D-proline (6404-31-5) → (2R)-2-carbamoyl-pyrrolidine-1-carboxylic acid benzyl ester (62937-47-7,58274-22-9)

Guidance literature:

Z-D-proline; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;

With ammonium hydroxide; In tetrahydrofuran; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.orglett.9b04033

Reference yield:

N-benzyloxycarbonyl-D-proline acid chloride (61350-62-7) → (2R)-2-carbamoyl-pyrrolidine-1-carboxylic acid benzyl ester (62937-47-7,58274-22-9)

Guidance literature:

With ammonia; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 16.16h; Product distribution / selectivity;

upstream raw materials:

pyrrolidine-2-carboxylic acid amide

Z-D-proline

benzyl chloroformate

D-Prolin

Downstream raw materials:

(-)-(R)-2-aminomethylpyrrolidine

(R,E)-benzyl 2-(((dimethylamino)methylene)carbamoyl)pyrrolidine-1-carboxylate

(R)-benzyl 2-(2-(4-chlorobenzyl)-5-methyl-2H-1,2,4-triazol-3-yl)pyrrolidine-1-carboxylate

(R)-benzyl 2-(4-methylthiazol-2-yl)pyrrolidine-1-carboxylate

Refernces

• 1、 -. "INHIBITORS OF PLASMA KALLIKREIN AND USES THEREOF". Paragraph 00319; 00320; 00337. . Retrieved 2019/02/17.
• 2、 -. "Macrocyclic MCL-1 inhibitors and methods of use". Paragraph 0907. . Retrieved 2019/02/28.