Fmoc-L-hydroxyproline Chemical Properties

Melting point:

189-193 °C

Boiling point:

595.5±50.0 °C(Predicted)

Density 

1.407±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

Powder

pka

3.74±0.40(Predicted)

color 

White to off-white

optical activity

[α]20/D 60±2°, c = 1% in methanol

BRN 

4574378

InChI

InChI=1S/C20H19NO5/c22-12-9-18(19(23)24)21(10-12)20(25)26-11-17-15-7-3-1-5-13(15)14-6-2-4-8-16(14)17/h1-8,12,17-18,22H,9-11H2,(H,23,24)/t12-,18+/m1/s1

InChIKey

GOUUPUICWUFXPM-XIKOKIGWSA-N

SMILES

N1(C(OCC2C3=C(C=CC=C3)C3=C2C=CC=C3)=O)C[C@H](O)C[C@H]1C(O)=O

CAS DataBase Reference

88050-17-3(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

Fmoc-L-hydroxyproline Usage And Synthesis

Chemical Properties

Light brown solid

Uses

peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

The general procedure for the synthesis of Fmoc-L-hydroxyproline from methyl 9-fluorenyl chloroformate and L-hydroxyproline is as follows: Example 2: Synthesis of (2S,4R)-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid 1. Sodium bicarbonate (80 g) and water (400 ml) were added to a solution of tetrahydrofuran (THF, 200 ml) containing (2S,4R)-4-hydroxy-L-proline (100 g) at 25-30 °C. 2. A solution of 9-fluorenylmethoxycarbonyl (Fmoc) chloride (226 g) dissolved in 200 ml of THF was added slowly. 3. The reaction mixture was stirred continuously at 25-30°C for 10-12 hours until the reaction was complete. 4. Upon completion of the reaction, the reaction was terminated by the addition of an appropriate amount of water. 5. The reaction mixture was washed with diisopropyl ether (DIPE) and subsequently acidified with 1N hydrochloric acid. 6. The acidified mixture was continued to be stirred for 2-3 hours to promote precipitation of the product. 7. The solid product was collected by filtration to give 150 g of Fmoc-L-hydroxyproline as a white solid. Product Characterization: 1H NMR (300 MHz, DMSO-d6): δ 1.89-2.24 (m, 2H), 3.34-3.43 (m, 2H), 3.43-3.54 (m, 0.5H), 4.12-4.21 (m, 3H), 4.25 (s, 2H), 4.28-4.42 (m, 0.5H), 5.16 (brs, 1H) , 7.29-7.34 (m, 2H), 7.38-7.65 (m, 2H), 7.63-7.65 (m, 2H). Melting point: 188-190°C. Mass spectrum (M + H): 354.33.

References

[1] Tetrahedron Letters, 1994, vol. 35, # 51, p. 9509 - 9512
[2] Angewandte Chemie - International Edition, 2009, vol. 48, # 10, p. 1784 - 1787
[3] Patent: US9518048, 2016, B2. Location in patent: Page/Page column 24

Fmoc-L-hydroxyproline(88050-17-3)Related Product Information

• cis-4-Hydroxy-L-proline
• L-Hydroxyproline
• N-Vinyl-2-pyrrolidone
• Fmoc-Phe-OH
• D-Proline
• Pyrrolidine
• Fmoc-Lys(Boc)-OH
• Boc-Hyp-OH
• Fmoc-Aib-OH
• N-Methyl-2-pyrrolidone
• 9-Fluorenylmethyl chloroformate
• CHLOROPHOSPHONAZO III
• Polyvinylpyrrolidone
• L-Proline
• L-PROLINE-(4-3H(N))
• cis-4-Hydroxy-D-proline
• Fmoc-OSu
• Fmoc-L-glutamic acid