| Identification | More | [Name]
FMOC-D-PIPECOLIC ACID | [CAS]
101555-63-9 | [Synonyms]
(2R)-1-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]HEXAHYDROPYRIDINE-2-CARBOXYLIC ACID
(2R)-1-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]PIPERIDINE-2-CARBOXYLIC ACID
D-1-FMOC-PIPECOLINIC ACID
(D)-N-(9-FLUORENYLMETHYLOXYCARBONYL)PIPECOLIC ACID
(D)-N-FMOC-PIPECOLIC ACID
FMOC-D-HOMOPROLINE
FMOC-D-HOMOPRO-OH
FMOC-D-HOPRO-OH
FMOC-D-PIC(2)-OH
FMOC-D-(+)-PIPECOLIC ACID
FMOC-D-PIPECOLIC ACID
FMOC-D-PIP-OH
FMOC-(R)-PIPECOLINIC ACID
FMOC-(R)-(+)-PIPERIDINE-2-CARBOXYLIC ACID
FMOC-(R)-PIPERIDINE-2-CARBOXYLIC ACID
N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-D-HOMOPROLINE
N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-D-PIPECOLIC ACID
N-ALPHA-FMOC-D-PIPECOLIC ACID
N-FMOC-D-PIPECOLINIC ACID
N-FMOC-(R)-PIPECOLINIC ACID | [Molecular Formula]
C21H21NO4 | [MDL Number]
MFCD00235899 | [Molecular Weight]
351.4 | [MOL File]
101555-63-9.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [Melting point ]
149-153°C | [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 ]
Solid | [pka]
3.97±0.20(Predicted) | [color ]
White to pale brown | [Optical Rotation]
20.768°(C=0.01g/ml DMF) | [BRN ]
5485101 | [Major Application]
peptide synthesis | [InChI]
1S/C21H21NO4/c23-20(24)19-11-5-6-12-22(19)21(25)26-13-18-16-9-3-1-7-14(16)15-8-2-4-10-17(15)18/h1-4,7-10,18-19H,5-6,11-13H2,(H,23,24)/t19-/m1/s1 | [InChIKey]
CKLAZLINARHOTG-LJQANCHMSA-N | [SMILES]
OC(=O)[C@H]1CCCCN1C(=O)OCC2c3ccccc3-c4ccccc24 | [CAS DataBase Reference]
101555-63-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [RIDADR ]
3077 | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29333990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powde | [Uses]
(R)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic Acid is a building block used as a reactant in the preparation cyclic tetrapeptide derivatives as histone deacetylase inhibitors and antitumor agents. | [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% 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. Upon completion of the reaction, water was added and the aqueous layer was extracted with ethyl acetate.
4. The aqueous layer was acidified to pH=2 by adding concentrated hydrochloric acid.
5. The acidified aqueous layer was extracted with ethyl acetate (3 x 40 mL). 6.
6. The organic phases were combined and washed sequentially with 1N HCl and brine, then dried with anhydrous magnesium sulfate and concentrated in vacuum to obtain a colorless oily liquid.
7. The oily liquid was dissolved in ether and cooled to give a fluffy white solid, which was washed with hexane and dried to give (S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (8.2 g, 38.7 mmol, 83% yield).
Product characterization data:
- TLC (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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