4-Sulfanyl-L-proline--hydrogen chloride (1/1)

Base Information

• Chemical Name: 4-Sulfanyl-L-proline--hydrogen chloride (1/1)
• CAS No.: 78854-27-0
• Molecular Formula: C5H10ClNO2S
• Molecular Weight: 147.2
• DSSTox Substance ID: DTXSID90705214
• Mol file: 78854-27-0.mol

Synonyms:SCHEMBL5666325;DTXSID90705214;4-Sulfanyl-L-proline--hydrogen chloride (1/1)

Chemical Property of 4-Sulfanyl-L-proline--hydrogen chloride (1/1)

Chemical Property:

• PSA: 88.13000
• LogP: 0.86210
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 183.0120774
• Heavy Atom Count: 10
• Complexity: 128

Purity/Quality:

99.3% ^*data from raw suppliers

(4S)-4-Mercapto-L-prolinechloride 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(CNC1C(=O)O)S.Cl
• Isomeric SMILES: C1[C@H](NCC1S)C(=O)O.Cl

Technology Process of 4-Sulfanyl-L-proline--hydrogen chloride (1/1)

There total 4 articles about 4-Sulfanyl-L-proline--hydrogen chloride (1/1) 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: 62.0%

4(S)-(benzylthio)pyrrolidine-2(S)-carboxylic acid hydrochloride (78854-26-9) → (4S)-4-mercapto-L-proline hydrochloride (78854-27-0)

Guidance literature:

With ammonia; sodium; for 3h;

DOI:10.1021/jo00334a015

Reference yield:

N-acetyl-4(S)-(benzylthio)pyrrolidine-2(S)-carboxic acid (78854-23-6) → (4S)-4-mercapto-L-proline hydrochloride (78854-27-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 3N HCl / H₂O / 8 h / Heating

2: 62 percent / Na, liq. NH₃ / 3 h

With hydrogenchloride; ammonia; sodium; In water;

DOI:10.1021/jo00334a015

Reference yield:

methyl N-acetyl-4(S)-(benzylthio)pyrrolidine-2(S)-carboxylate (78854-22-5) → (4S)-4-mercapto-L-proline hydrochloride (78854-27-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1N aq. NaOH / methanol / 16 h / 0 °C

2: 90 percent / 3N HCl / H₂O / 8 h / Heating

3: 62 percent / Na, liq. NH₃ / 3 h

With hydrogenchloride; sodium hydroxide; ammonia; sodium; In methanol; water;

DOI:10.1021/jo00334a015

upstream raw materials:

4(S)-(benzylthio)pyrrolidine-2(S)-carboxylic acid hydrochloride

N-acetyl-4(S)-(benzylthio)pyrrolidine-2(S)-carboxic acid

methyl N-acetyl-4(S)-(benzylthio)pyrrolidine-2(S)-carboxylate

(3R,5S)-5-(methoxycarbonyl)-1-acetylpyrrolidin-3-yl 4-methylbenzenesulfonate

Downstream raw materials:

(2S,4S)-4-(benzylsulfanyl)-pyrrolidine-2-carboxylic acid

(4S)-4-(4-cyclohexylbenzylthio)-L-proline

(4S)-(4-tert-butyl)benzylthio-L-proline

Refernces