cis-1-benzoyl-4-((4-methylsulfonyl)oxy)-L-proline

Base Information

• Chemical Name: cis-1-benzoyl-4-((4-methylsulfonyl)oxy)-L-proline
• CAS No.: 120807-02-5
• Molecular Formula: C13H15 N O6 S
• Molecular Weight: 313.331
• European Community (EC) Number: 416-040-0,601-740-2,603-319-9
• DSSTox Substance ID: DTXSID20923565
• Nikkaji Number: J775.978I
• Wikidata: Q76416679
• Mol file: 120807-02-5.mol

Synonyms:120807-02-5;cis-1-benzoyl-4-((4-methylsulfonyl)oxy)-L-proline;EC 416-040-0;(4S)-N-BENZOYL-4-(MESYLOXY)-L-PROLINE;(2S,4S)-1-benzoyl-4-methylsulfonyloxypyrrolidine-2-carboxylic acid;cis-1-benzoyl-4-[(4-methylsulfonyl)oxy]-L-proline;cis-1-Benzoyl-4-mesyloxy-L-proline;129155-63-1;SCHEMBL10467900;DTXSID20923565;ZLUIBJGFQFHEPT-QWRGUYRKSA-N;AKOS022180568;(cis)-1-benzoyl-4-mesyloxy-L-proline;1-Benzoyl-4-[(methanesulfonyl)oxy]proline;1-Benzoyl-4alpha-(methylsulfonyloxy)-L-proline;(2S,4S)-1-BENZOYL-4-(METHANESULFONYLOXY)PYRROLIDINE-2-CARBOXYLIC ACID

Chemical Property of cis-1-benzoyl-4-((4-methylsulfonyl)oxy)-L-proline

Chemical Property:

• Melting Point: 172-173 °C
• Refractive Index: 1.61
• Boiling Point: 591.7±50.0 °C(Predicted)
• PKA: 3.76±0.10(Predicted)
• PSA: 109.36000
• Density: 1.48±0.1 g/cm3(Predicted)
• LogP: 1.34920
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 313.06200837
• Heavy Atom Count: 21
• Complexity: 505

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Statements: 52/53
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)(=O)OC1CC(N(C1)C(=O)C2=CC=CC=C2)C(=O)O
• Isomeric SMILES: CS(=O)(=O)O[C@H]1C[C@H](N(C1)C(=O)C2=CC=CC=C2)C(=O)O

Technology Process of cis-1-benzoyl-4-((4-methylsulfonyl)oxy)-L-proline

There total 3 articles about cis-1-benzoyl-4-((4-methylsulfonyl)oxy)-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: 84.0%

methanesulfonic acid (75-75-2,98527-29-8) + (2S,4R)-1-benzoyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester (31560-20-0,120806-96-4) → N-benzoyl-4-trans-(methanesulfonyloxy)-L-proline (129155-63-1) + N-benzoyl-4-cis-(methanesulfonyloxy)-L-proline (120807-02-5)

Guidance literature:

With di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine; In toluene; at 60 - 70 ℃; Yields of byproduct given;

DOI:10.1021/jo9609539

Reference yield:

methanesulfonic acid (75-75-2,98527-29-8) + di-isopropyl azodicarboxylate (2446-83-5) + (2S,4R)-1-benzoyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester (31560-20-0,120806-96-4) + triphenylphosphine (603-35-0) → N-benzoyl-4-trans-(methanesulfonyloxy)-L-proline (129155-63-1) + N-benzoyl-4-cis-(methanesulfonyloxy)-L-proline (120807-02-5) + Triphenylphosphine oxide (791-28-6) + ytriphenylphosphine oxide - diisopropyl hydrazinedicarboxylate

Guidance literature:

With triethylamine; In toluene; at 60 - 70 ℃; Product distribution;

DOI:10.1021/jo9609539

Reference yield:

5-aza-5-benzoyl-2-oxa-3-oxo-bicyclo<2.2.1>heptane (31560-25-5) + methanesulfonyl chloride (124-63-0) → N-benzoyl-4-cis-(methanesulfonyloxy)-L-proline (120807-02-5)

Guidance literature:

Multistep reaction;

DOI:10.1016/S0040-4039(00)88775-4

upstream raw materials:

5-aza-5-benzoyl-2-oxa-3-oxo-bicyclo<2.2.1>heptane

methanesulfonyl chloride

methanesulfonic acid

(2S,4R)-1-benzoyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester

Downstream raw materials:

(2S,4R)-1-Benzoyl-4-chloro-pyrrolidine-2-carboxylic acid

(2S,4S)-1-Benzoyl-4-chloro-pyrrolidine-2-carboxylic acid

(2S,4S)-1-Benzoyl-4-phenyl-pyrrolidine-2-carboxylic acid