N-Carbobenzyloxy-4-keto-L-proline

Base Information

• Chemical Name: N-Carbobenzyloxy-4-keto-L-proline
• CAS No.: 64187-47-9
• Molecular Formula: C13H13NO5
• Molecular Weight: 263.25
• Hs Code.: 2933990090
• European Community (EC) Number: 693-311-1
• DSSTox Substance ID: DTXSID30454390
• Nikkaji Number: J2.074.393J
• Wikidata: Q72515268
• Mol file: 64187-47-9.mol

Synonyms:64187-47-9;N-Carbobenzyloxy-4-keto-L-proline;N-Carbobenzoxy-4-oxo-L-proline;(S)-1-((Benzyloxy)carbonyl)-4-oxopyrrolidine-2-carboxylic acid;(S)-1-(benzyloxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid;N-Cbz-4-keto-L-proline;(2S)-4-oxo-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid;(S)-1-Z-4-OXOPYRROLIDINE-2-CARBOXYLIC ACID;N-cbz-4-ketoproline;SCHEMBL636520;DTXSID30454390;N-Carbobenzyloxy-4-keto-l-prolne;(2S)-1-benzyloxycarbonyl-4-oxo-pyrrolidine-2-carboxylic acid;(2S)-1-[(benzyloxy)carbonyl]-4-oxopyrrolidine-2-carboxylic acid;AMY36700;MFCD07367987;AKOS015836800;CS-W010137;1-benzyloxycarbonyl-4-keto-(S)-proline;1-[(Benzyloxy)carbonyl]-4-oxoproline #;AC-14421;AS-31286;1-(Benzyloxycarbonyl)-4-keto-(S)-proline;A8808;4-keto-1-[(phenylmethoxy)carbonyl]-L-proline;EN300-1086676;(S)-1-Z-4-oxopyrrolidine-2-carboxylic acid, 97%;J-523531;1-(benzyloxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid;(2S)-4-Oxopyrrolidine-1,2alpha-dicarboxylic acid 1-benzyl ester

Chemical Property of N-Carbobenzyloxy-4-keto-L-proline

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 95℃
• Refractive Index: 1.597
• Boiling Point: 488.455 °C at 760 mmHg
• Flash Point: 249.209 °C
• PSA: 83.91000
• Density: 1.409 g/cm³
• LogP: 0.98910
• Storage Temp.: 2-8°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 263.07937252
• Heavy Atom Count: 19
• Complexity: 375

Purity/Quality:

99% ^*data from raw suppliers

(S)-1-Z-4-oxopyrrolidine-2-carboxylic acid 97% ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(N(CC1=O)C(=O)OCC2=CC=CC=C2)C(=O)O
• Isomeric SMILES: C1[C@H](N(CC1=O)C(=O)OCC2=CC=CC=C2)C(=O)O

Technology Process of N-Carbobenzyloxy-4-keto-L-proline

There total 7 articles about N-Carbobenzyloxy-4-keto-L-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: 100.0%

(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (13504-85-3) → 1-benzyloxycarbonyl-4-keto-L-proline (64187-47-9)

Guidance literature:

With Jones reagent; In acetone; for 12h; Cooling with ice;

DOI:10.1016/j.tetlet.2016.09.032

Reference yield: 82.0%

4R-4-hydroxyproline (51-35-4,30724-02-8) → 1-benzyloxycarbonyl-4-keto-L-proline (64187-47-9)

Guidance literature:

Reference yield: 79.0%

N-(benzyloxycarbonyl)succinimide (75315-63-8) + 4R-4-hydroxyproline (51-35-4,30724-02-8) → 1-benzyloxycarbonyl-4-keto-L-proline (64187-47-9)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; triethylamine; In tetrahydrofuran; water; at 0 - 25 ℃; pH=8 - 9; Reagent/catalyst; Temperature; Large scale;

upstream raw materials:

(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

benzyl chloroformate

4R-4-hydroxyproline

N-(benzyloxycarbonyl)succinimide

Downstream raw materials:

4-oxo-L-proline

(2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline

(2S)-4-oxo-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid tert-butyl ester

N-carbobenzyloxy-cis-4-hydroxy-trans-4-phenyl-L-proline

Refernces

• 1、 -. "Synthesis of 4 - oxo - L - proline derivatives (by machine translation)". Paragraph 0088; 0091; 0092; 0093; 0094; 0095; 0097; 0098. . Retrieved 2018/11/03.
• 2、 Evitt, Andrew S.,Cox, Russell J.. "Synthesis and evaluation of conformationally restricted inhibitors of aspartate semialdehyde dehydrogenase". scheme or table. p. 1564 - 1575. Retrieved 2012/03/27.