(S)-proglumide

Base Information

• Chemical Name: (S)-proglumide
• CAS No.: 32999-84-1
• Molecular Formula: C18H26 N2 O4
• Molecular Weight: 0
• DSSTox Substance ID: DTXSID501317356
• Nikkaji Number: J232.200E
• Wikidata: Q27145840
• Mol file: 32999-84-1.mol

Synonyms:(S)-proglumide;32999-84-1;(4S)-4-benzamido-5-(dipropylamino)-5-oxopentanoic acid;(S)-4-Benzamido-5-(dipropylamino)-5-oxopentanoic acid;(+)-Proglumide;starbld0015742;CHEBI:76268;DTXSID501317356;N(2)-benzoyl-N,N-dipropyl-L-alpha-glutamine;Q27145840

Chemical Property of (S)-proglumide

Chemical Property:

• PSA: 86.71000
• LogP: 2.68930
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 334.18925731
• Heavy Atom Count: 24
• Complexity: 413

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCN(CCC)C(=O)C(CCC(=O)O)NC(=O)C1=CC=CC=C1
• Isomeric SMILES: CCCN(CCC)C(=O)[C@H](CCC(=O)O)NC(=O)C1=CC=CC=C1

Technology Process of (S)-proglumide

There total 11 articles about (S)-proglumide 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: 75.0%

benzoyl chloride (98-88-4) + H-Glu-NPr2 (118884-82-5) → 5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid (32999-84-1,24485-90-3)

Guidance literature:

With sodium hydrogencarbonate; In diethyl ether; water; for 3h;

DOI:10.1248/cpb.36.3433

Reference yield:

proglumide (6620-60-6,24485-90-3) → 5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid (32999-84-1,24485-90-3) + 5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid (32999-90-9,24485-90-3)

Guidance literature:

With MCCD-HPS packed column; In hydrogenchloride; acetonitrile; pH=8.6;

DOI:10.1021/ac0204909

Reference yield:

N-benzyloxycarbonyl-L-glutamic acid (1155-62-0) → 5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid (32999-84-1,24485-90-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 89.9 g / p-toluenesulfonic acid hydrate / benzene

2: 44 percent / tetrahydrofuran / 8 h / Heating

3: 3.2 g / H₂ / 10percent Pd-C / methanol / 3 h / Ambient temperature

4: NaHCO₃ / H₂O; diethyl ether / 3 h

With hydrogen; sodium hydrogencarbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; water; benzene;

DOI:10.1248/cpb.36.3961

upstream raw materials:

benzoyl chloride

H-Glu-NPr₂

methanol

proglumide

Refernces

• 1、 -. "Method for preparing chiral proglumide and pharmaceutical composition". Paragraph 0042; 0044. . Retrieved 2017/05/02.
• 2、 Muralidhar,Chirumamilla,Ramachandran,Marchant,Nigam. "Resolution of (RS)-proglumide using lipase from Candida cylindraceae.". . p. 1471 - 1475. Retrieved 2007/10/03.