Z-TRANS-4-HYDROXY-L-PROLINOL Chemical Properties

Boiling point:

240 °C(lit.)

Density 

1.297 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.547(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

form 

clear liquid

pka

14.56±0.40(Predicted)

color 

Colorless to Light orange to Yellow

optical activity

[α]20/D 33°, c = 15 in chloroform

InChI

InChI=1S/C13H17NO4/c15-8-11-6-12(16)7-14(11)13(17)18-9-10-4-2-1-3-5-10/h1-5,11-12,15-16H,6-9H2/t11-,12+/m0/s1

InChIKey

WDEQGLDWZMIMJM-NWDGAFQWSA-N

SMILES

N1(C(OCC2=CC=CC=C2)=O)C[C@H](O)C[C@H]1CO

Safety Information

Hazard Codes 

Xi

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933998090

Z-TRANS-4-HYDROXY-L-PROLINOL Usage And Synthesis

Uses

peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

N-Benzyloxycarbonyl-(4R)-hydroxy-L-proline (150 g, 0.565 mol) was used as a raw material, which was dissolved in tetrahydrofuran (1.5 L), and the borane-dimethyl sulfide complex (59.0 ml, 0.622 mol) was added dropwise slowly under stirring at 0 °C. After the dropwise addition, the reaction mixture was heated to reflux and stirred continuously for 3 hours. Subsequently, the reaction mixture was cooled to 0 °C and borane-dimethyl sulfide complex (16.1 ml, 0.170 mol) was added again and stirring was continued for 10 hours. After completion of the reaction, the reaction mixture was cooled and water (500 ml) was added slowly at 0 °C to quench the excess borane-dimethyl sulfide complex. The reaction mixture was extracted with a solvent mixture of ethyl acetate and chloroform-methanol (10:1, v/v), the organic phases were combined, washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to afford Cbz-(2S,4R)-4-hydroxyprolinol (122.06 g, 86% yield), the product was a pale yellow oil, which could be used for subsequent reactions without further purification.1H-NMR (CDCl3) δ: 1.52-1.81 (m, 3H), 2.06 (m, 1H), 3.40-3.85 and 4.04- 4.61 (m series, total 6H), 5.15 (s, 2H, ArCH2), 7.20-7.44 (m, 5H, Ar).

References

[1] Patent: EP1623975, 2006, A1. Location in patent: Page/Page column 20-21
[2] Heterocycles, 1984, vol. 22, # 12, p. 2735 - 2738
[3] Tetrahedron, 2006, vol. 62, # 10, p. 2321 - 2330
[4] Nucleosides, Nucleotides and Nucleic Acids, 2003, vol. 22, # 5-8, p. 1285 - 1288
[5] Journal of Medicinal Chemistry, 2004, vol. 47, # 5, p. 1161 - 1174

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