| Identification | More | [Name]
(S)-N-BOC-Propargylglycine | [CAS]
63039-48-5 | [Synonyms]
BOC-L-PROPARGYLGLYCINE
RARECHEM BK PT 0256
(S)-N-BOC-PROPARGYLGLYCINE
(S)-N-TERT-BUTOXYCARBONYL-2-AMINO-4-PENTYNOIC ACID
(S)-N-(TERT-BUTOXYCARBONYL)-PROPARGYLGLYCINE
Boc-Gly(propargyl)-OH
(S)-N-Boc-propargylglycine(e.e.)
L-TERT-BUTOXYCARBONYL-L-PROPARGYL GLYCINE
BOC-2-PROPARGYL-L-GLYCINOL
N-BOC-2-PROPARGYL-L-GLYCINE
L-2-Propargylglycine, N-BOC protected
(S)-(1-Hydroxymethyl-but-3-ynyl)-carbamic acid tert-butyl ester
(S)-2-tert-Butoxycarbonylamino-pent-4-ynoic acid
Boc-Pra-OH
(2S)-2-(tert-butoxycarbonylamino)pent-4-ynoate
Boc-L-Propargylglycine.DCHA
(S)-N-Boc-propargylglycine, 95%, ee:98%
(S)-N-BOC-Propargylglycine, 98% ee | [Molecular Formula]
C10H15NO4 | [MDL Number]
MFCD01320855 | [Molecular Weight]
213.23 | [MOL File]
63039-48-5.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white to light yellow crystalline powder | [Melting point ]
85.5 °C | [Boiling point ]
353.22°C (rough estimate) | [density ]
1.2177 (rough estimate) | [refractive index ]
1.4368 (estimate) | [storage temp. ]
Store at 0°C | [form ]
Crystalline Powder | [pka]
3.53±0.10(Predicted) | [color ]
Off-white to light yellow | [Optical Rotation]
[α]/D 26.0±2.0°, c = 1 in methanol | [Water Solubility ]
Soluble in water. | [BRN ]
5739897 | [Major Application]
peptide synthesis | [InChI]
InChI=1S/C10H15NO4/c1-5-6-7(8(12)13)11-9(14)15-10(2,3)4/h1,7H,6H2,2-4H3,(H,11,14)(H,12,13)/t7-/m0/s1 | [InChIKey]
AMKHAJIFPHJYMH-ZETCQYMHSA-N | [SMILES]
C(O)(=O)[C@@H](NC(OC(C)(C)C)=O)CC#C | [CAS DataBase Reference]
63039-48-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38 | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3 | [HazardClass ]
IRRITANT | [HS Code ]
29241990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Skin Sens. 1 |
| Hazard Information | Back Directory | [Chemical Properties]
off-white to light yellow crystalline powder | [Uses]
N-Boc-2-propargyl-L-glycine is used as pharmaceutical intermediate. | [reaction suitability]
reaction type: Boc solid-phase peptide synthesis
reaction type: click chemistry | [Synthesis]
Step 5: Synthesis of Boc-L-ynylglycine
L-alkynylglycine (10 g) [prepared according to Schwyzer et al. Helv. Chim. Acta, 59, 2181 (1976)] was suspended in tetrahydrofuran (30 mL). To this suspension, water (30 mL), potassium carbonate (36.7 g) and di-tert-butyl dicarbonate (21.9 g) were added sequentially. Subsequently, additional water was added to completely dissolve the mixture and the reaction mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, the organic solvent was removed by evaporation. The resulting aqueous solution was first washed with ether and then acidified with aqueous 1N citric acid to pH 3. The acidified solution was extracted with dichloromethane, and the extract was evaporated to remove the solvent to afford Boc-L-alkynylglycine (18.9 g, 97% yield), which was used in subsequent steps without further purification. | [References]
[1] Chemistry - An Asian Journal, 2010, vol. 5, # 8, p. 1765 - 1769
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7512 - 7515
[3] Patent: US5212185, 1993, A
[4] Patent: US5298505, 1994, A
[5] Patent: US5373017, 1994, A |
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