FMOC-L-PIPECOLIC ACID Chemical Properties

Melting point:

149-153

Boiling point:

561.6±43.0 °C(Predicted)

Density 

1.293±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

soluble in Methanol

form 

powder to crystal

pka

3.97±0.20(Predicted)

color 

White to Light yellow

optical activity

[α]22/D 23°, c = 1 in DMF

BRN 

4718405

CAS DataBase Reference

86069-86-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

50/53

Safety Statements 

60-61

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

FMOC-L-PIPECOLIC ACID Usage And Synthesis

Chemical Properties

White powder

Uses

peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

The general procedure for the synthesis of (R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid from the compound (CAS: 102774-86-7) and L-2-piperidinic acid is as follows: 1. L-piperidine acid (3.6 g, 38.7 mmol) was dissolved in 40 mL of 10% aqueous sodium carbonate solution in a round-bottomed flask and stirred at room temperature for 5 min. 2. Fmoc-OSu (8.5 g, 34.8 mmol) dissolved in 35 mL of dioxane was added to the above solution and the reaction mixture was stirred overnight. 3. After completion of the reaction, water was added and the aqueous layer was extracted with ethyl acetate. 4. The aqueous layer was adjusted to pH=2 by adding concentrated hydrochloric acid and then extracted with ethyl acetate (3 x 40 mL). 5. The organic phases were combined, washed sequentially with 1N hydrochloric acid and saturated brine, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a colorless oily liquid. 6. The oily liquid was dissolved in ether, cooled and precipitated as a fluffy white solid, washed with hexane and dried to afford (S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (8.2 g, 38.7 mmol, 83% yield). Product Characterization Data: - TLC (unfolding agent: hexane:EtOAc:TFA = 1:1:0.2): rf = 0.60 - HPLC (gradient A): retention time = 24.6-24.8 min - 1H NMR (300 MHz, CDCl3): δ 1.28-1.53 (m, 2H), 1.69-1.82 (m, 3H), 2.19-2.37 (m, 1H), 3.15 (t, 1H, J = 13.2 Hz), 4.05-4.33 (m, 2H), 4.37-4.49 (m, 2H), 4.76- 5.05 (m, 1H), 7.28-7.41 (m, 4H), 7.55-7.62 (m, 2H), 1.77 (s, 2H) - 13C NMR (75 MHz, CDCl3): δ 20.72, 24.70, 26.55, 41.94, 47.25, 54.19, 67.86, 119.97, 125.08, 127.07, 127.68, 141.33, 143.89, 156.65, 177.36 - MS (ESI): m/z 352.66 [M + H]+, calculated 352.40 [M + H]+

References

[1] Patent: WO2013/91900, 2013, A1. Location in patent: Page/Page column 41

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