L-Proline, 4-hydroxy-, methyl ester, (4S)- (9CI)

Base Information

• Chemical Name: L-Proline, 4-hydroxy-, methyl ester, (4S)- (9CI)
• CAS No.: 81102-38-7
• Molecular Formula: C6H11NO3
• Molecular Weight: 145.158
• Mol file: 81102-38-7.mol

Synonyms:D-Proline,4-hydroxy-,methyl ester,(4S);

Chemical Property of L-Proline, 4-hydroxy-, methyl ester, (4S)- (9CI)

Chemical Property:

• Boiling Point: 247.2 °C at 760 mmHg
• Flash Point: 103.3 °C
• PSA: 58.56000
• Density: 1.216 g/cm³
• LogP: -0.78900

Purity/Quality:

99.90% ^*data from raw suppliers

(2S,4S)-METHYL 4-HYDROXYPYRROLIDINE-2-CARBOXYLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Proline, 4-hydroxy-, methyl ester, (4S)- (9CI)

There total 9 articles about L-Proline, 4-hydroxy-, methyl ester, (4S)- (9CI) 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: 99.0%

methanol (67-56-1) + hydroxy L-proline (618-27-9,30724-02-8) → cis-L-hydroxyproline methyl ester (81102-38-7,775275-31-5,790644-51-8,754962-86-2)

Guidance literature:

methanol; With thionyl chloride; at 0 ℃; for 0.5h;

hydroxy L-proline; at 20 ℃; for 50h;

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → cis-L-hydroxyproline methyl ester (81102-38-7,775275-31-5,790644-51-8,754962-86-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / Et₃N / CHCl₃ / 0 °C

2: 1.) PPh₃, DEAD, PhCO₂H; 2.) KOH / 1.) toluene; 2.) MeOH

3: HCO₂H / 1,2-dichloro-ethane

With potassium hydroxide; formic acid; triethylamine; triphenylphosphine; benzoic acid; diethylazodicarboxylate; In chloroform; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4039(97)10793-6

Reference yield:

(3S,5S)-5-Iodomethyl-3-((S)-1-phenyl-ethylamino)-dihydro-furan-2-one (176966-58-8) → cis-L-hydroxyproline methyl ester (81102-38-7,775275-31-5,790644-51-8,754962-86-2)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol; for 5h; under 1861.7 Torr; Ambient temperature;

DOI:10.1016/0957-4166(96)00079-1

upstream raw materials:

(3S,5S)-5-Iodomethyl-3-((S)-1-phenyl-ethylamino)-dihydro-furan-2-one

(2S,4S)-methyl 4-hydroxy-1-tritylpyrrolidine-2-carboxylate

L-4-hydroxyproline methyl ester hydrochloride

methyl (2S,4R)-4-hydroxy-1-tritylpyrrolidine-2-carboxylate

Downstream raw materials:

hydroxy L-proline

N-((3R,5R)-5-fluoropiperidin-3-yl)benzamide

N-((3R,5R)-5-fluoro-1-tritylpiperidin-3-yl)benzamide

N-((3R,5S)-5-(hydroxymethyl)-1-tritylpyrrolidin-3-yl)benzamide

Refernces

• 1、 -. "CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE". Paragraph 00576-00578; 00582-00583. . Retrieved 2019/06/11.
• 2、 Owens, Neil W.,Lee, Adrian,Marat, Kirk,Schweizer, Frank. "The implications of (2S,4S)-hydroxyproline 4-O-glycosylation for prolyl amide isomerization". experimental part. p. 10649 - 10657. Retrieved 2010/05/19.