N-Cbz-Hydroxy-L-proline Chemical Properties

Melting point:

104-107 °C

Boiling point:

486.9±45.0 °C(Predicted)

Density 

1.416±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Dichloromethane, Ethyl Acetate

form 

Oil

pka

3.78±0.40(Predicted)

color 

White to off-white

optical activity

[α]20/D 54±1°, c = 2% in ethanol

Water Solubility 

Slightly soluble in water.

BRN 

90295

CAS DataBase Reference

13504-85-3(CAS DataBase Reference)

Safety Information

WGK Germany 

3

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

N-Cbz-Hydroxy-L-proline Usage And Synthesis

Chemical Properties

Viscous Oil

Uses

A competitive inhibitor of porcine kidney prolidase.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

GENERAL METHOD: To a solution of L-hydroxyproline (78.7 g, 600 mmol) and sodium bicarbonate (126 g, 1.5 mol) in water (900 mL), a solution of benzyl chloroformate (89.6 mL, 630 mmol) in dioxane (90 mL) was slowly added. The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction (monitored by thin-layer chromatography), the reaction mixture was cooled to 0 °C in an ice bath and acidified to pH 2 with 12 M hydrochloric acid (about 75 mL was required). Subsequently, the aqueous phase was extracted with ethyl acetate (3 × 500 mL), the organic phases were combined and washed with saturated brine (3 × 200 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a colorless viscous oil. The yield was quantitative, and the product could be directly used in the next reaction without further purification.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 16, p. 1845 - 1847
[2] Angewandte Chemie - International Edition, 2007, vol. 46, # 47, p. 9073 - 9077
[3] Patent: EP1193270, 2002, A2. Location in patent: Page 14, 35-36, 105
[4] Tetrahedron Letters, 2016, vol. 57, # 44, p. 4882 - 4884
[5] Chemical and Pharmaceutical Bulletin, 2018, vol. 66, # 5, p. 575 - 580

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