trans-4-Hydroxy-L-proline methyl ester hydrochloride Chemical Properties

Melting point:

169 °C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated)

form 

Solid

color 

White to Off-White

BRN 

4716932

Stability:

Hygroscopic

InChI

InChI=1/C6H11NO3.ClH/c1-10-6(9)5-2-4(8)3-7-5;/h4-5,7-8H,2-3H2,1H3;1H/t4-,5+;/s3

InChIKey

KLGSHNXEUZOKHH-SRJSDOSHNA-N

SMILES

[C@@H]1(NC[C@H](O)C1)C(=O)OC.Cl |&1:0,3,r|

CAS DataBase Reference

40216-83-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29339900

trans-4-Hydroxy-L-proline methyl ester hydrochloride Usage And Synthesis

Chemical Properties

White Solid

Uses

trans-4-Hydroxy-L-proline (H952376) derivative. A natural constituent of animal structural proteins such as collagen and elastin.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

The general procedure for synthesizing trans-4-hydroxy-L-proline methyl ester hydrochloride from methanol and trans-4-hydroxy-L-proline hydrochloride is as follows: Example 1: (2S,4R)-4-hydroxy-2-pyrrolidine carboxylic acid hydrochloride (1.0 g, 7.6 mmol) was dissolved in methanol (25 mL) and cooled to 0°C. Thionyl chloride (0.83 mL, 11.4 mmol) was added slowly under stirring. The reaction mixture was gradually warmed to room temperature and subsequently heated to reflux overnight. After completion of the reaction, it was cooled to room temperature and the reaction mixture was concentrated to dryness under reduced pressure to afford trans-4-hydroxy-L-proline methyl ester hydrochloride (1.2 g, 92% yield) in white solid form. The structure of the product was confirmed by 1H NMR (300 MHz, DMSO-d6).

IC 50

Non-cleavable Linker

References

[1] Organic Letters, 2018, vol. 20, # 1, p. 162 - 165
[2] Patent: WO2013/174937, 2013, A1. Location in patent: Page/Page column 74
[3] Patent: US2015/152048, 2015, A1. Location in patent: Paragraph 0447-0448

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