N-Boc-trans-4-Hydroxy-L-proline methyl ester Chemical Properties

Melting point:

92-96 °C (lit.)

alpha 

-65 º (c=1 CHCl3)

Boiling point:

132°C/0.05mmHg(lit.)

Density 

1.216±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in chloroform, dichloromethane and ethyl acetate.

form 

Crystalline Powder

pka

14.27±0.40(Predicted)

color 

White to light beige

optical activity

[α]20/D -65°, c = 1% in chloroform

InChI

InChI=1S/C11H19NO5/c1-11(2,3)17-10(15)12-6-7(13)5-8(12)9(14)16-4/h7-8,13H,5-6H2,1-4H3/t7-,8+/m1/s1

InChIKey

MZMNEDXVUJLQAF-SFYZADRCSA-N

SMILES

N1(C(OC(C)(C)C)=O)C[C@H](O)C[C@H]1C(OC)=O

LogP

0.813 at 25℃

CAS DataBase Reference

74844-91-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

N-Boc-trans-4-Hydroxy-L-proline methyl ester Usage And Synthesis

Chemical Properties

Clear Colourless Oil

Uses

A potential iNOS inhibitor.

Uses

It is used in the synthesis of For-Met-Leu-Phe-OMe (fMLF-OMe) analogues based on Met residue replacement by 4-amino-proline scaffold.

Uses

(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic Acid 1-tert-Butyl Ester 2-Methyl Ester roline scaffold.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

The general procedure for the synthesis of N-Boc-trans-4-hydroxy-L-proline methyl ester from di-tert-butyl dicarbonate and trans-4-hydroxy-L-proline methyl ester hydrochloride was as follows: the trans-4-hydroxy-L-proline methyl ester hydrochloride (14.5 g, 0.1 mol) obtained in step I was suspended in CH2Cl2 (400 mL), cooled to 0 °C, and with stirring, sequentially Et3N (28 mL, 0.2 mol), DMAP (0.61 g, 5 mmol) and Boc anhydride (27.5 mL, 0.12 mol) were added. The reaction mixture was gradually warmed to room temperature and stirring was continued for 2 hours. After completion of the reaction, the solvent was removed by concentration under reduced pressure, ether was added to the residual solid, the solid was collected by filtration and washed well with ether. The filtrates were combined and concentrated under reduced pressure. The residue was dissolved in CH2Cl2, washed with saturated aqueous NaHCO3 and saturated aqueous NaCl in turn, and the organic phase was dried with anhydrous Na2SO4. The solvent was evaporated under reduced pressure to give a light yellow oil, which was solidified by high vacuum treatment. The resulting solid was ground several times with hexane and dried in high vacuum to obtain 1-tert-butyl-2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate as a white solid (24.5 g, 100% yield). The product characterization data were as follows:(M+1) 245; 1H NMR (CDCl3, 300MHz) δ 4.54-4.37 (m, 2H), 3.75 (s, 3H), 3.70-3.40 (m, 2H), 2.48-2.21 (m, 2H), 2.13-2.0 (m, 1H), 1.46 (s, 3H), 1.41 (s, 6H).

IC 50

Non-cleavable Linker

References

[1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 22, p. 5699 - 5702
[2] Patent: WO2007/113634, 2007, A1. Location in patent: Page/Page column 60-61
[3] Tetrahedron Asymmetry, 2009, vol. 20, # 12, p. 1433 - 1436
[4] Journal of Chemical Research, 2009, # 11, p. 668 - 670
[5] Tetrahedron Letters, 2012, vol. 53, # 30, p. 3847 - 3849

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