| Identification | More | [Name]
Boc-L-glutamic acid 1-tert-butyl ester | [CAS]
24277-39-2 | [Synonyms]
BOC-GLU-OBUT
BOC-GLU-OTBU
BOC-GLUTAMIC ACID-OTBU
BOC-L-GLU-OTBU
BOC-L-GLUTAMIC ACID 1-TERT-BUTYL ESTER
BOC-L-GLUTAMIC ACID ALPHA-T-BUTYL ESTER
N-ALPHA-T-BOC-L-GLU-ALPHA-T-BUTYL ESTER
N-ALPHA-T-BOC-L-GLUTAMIC ACID ALPHA-T-BUTYL ESTER
N-ALPHA-T-BUTOXYCARBONYL-L-GLUTAMIC ACID ALPHA-T-BUTYL ESTER
N-ALPHA-TERT-BUTYLOXYCARBONYL-L-GLUTAMIC ACID-ALPHA-TERT-BUTYL ESTER
N-T-BOC-L-GLUTAMIC ACID ALPHA-T-BUTYL ESTER
N-T-BUTOXYCARBONYL-L-GLUTAMIC ACID 1-T-BUTYL ESTER
N-TERT-BUTOXYCARBONYL-L-GLUTAMIC ACID 1-TERT-BUTYL ESTER
N-T-boc-L-glutamic acid A-T-butyl-ester
Boc-L-glutamic acid α-tert.butyl ester
N-ALPHA-T-BUTYLOXYCARBONYL-L-GLUTAMIC ACID-ALPHA-T-BUTYL ESTER
N-tert-Butoxycarbonyl-L-glutamic acid 2-tert-butyl ester
BOC-L-GLUTAMIC ACID A-T-BUTYLESTER
BOC-L-GLUTAMIC ACID 2-TERT.BUTYL ESTER
N-tert-Butoxycarbonyl-L-glutamic acid α-tert butyl ester | [Molecular Formula]
C14H25NO6 | [MDL Number]
MFCD00038273 | [Molecular Weight]
303.35 | [MOL File]
24277-39-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
111.0 to 115.0 °C | [Boiling point ]
449.8±40.0 °C(Predicted) | [density ]
1.121±0.06 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
Soluble in dimethyl formamide. | [form ]
powder to crystaline | [pka]
4.48±0.10(Predicted) | [color ]
White to Almost white | [Optical Rotation]
-30.8554° (C=1.0042 g/100ml, MEOH) | [BRN ]
3653769 | [InChI]
InChI=1S/C14H25NO6/c1-13(2,3)20-11(18)9(7-8-10(16)17)15-12(19)21-14(4,5)6/h9H,7-8H2,1-6H3,(H,15,19)(H,16,17)/t9-/m0/s1 | [InChIKey]
YMOYURYWGUWMFM-VIFPVBQESA-N | [SMILES]
C(OC(C)(C)C)(=O)[C@H](CCC(O)=O)NC(OC(C)(C)C)=O | [CAS DataBase Reference]
24277-39-2(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
White powder crystal | [Uses]
Boc-Glu-OtBu is an N-terminal protected amino acid used in solid-phase peptide synthesis (SPPS) to make unique peptides containing glutamate tert-butyl ester residues. | [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
General procedure for the synthesis of Boc-L-glutamic acid 1-tert-butyl ester from (S)-1-tert-butyl 5-methyl 2-((tert-butoxycarbonyl)amino)pentanedioate: crude N-Boc-glutamic acid 1-tert-butyl ester (5-methyl ester from the previous step, 30.4 g, 95.8 mmol) was dissolved in THF (300 mL), 1N LiOH was added aqueous solution (144 mL). The reaction mixture was stirred at room temperature for 40 min and the progress of the reaction was monitored by TLC to confirm complete consumption of the feedstock. Upon completion of the reaction, THF was removed using a rotary evaporator.The remaining aqueous phase was extracted with ethyl acetate (3 × 100 mL) and subsequently acidified with solid citric acid to pH 4. The acidified aqueous phase was again extracted with ethyl acetate (3 × 100 mL). All the ethyl acetate extracts were combined, washed with saturated brine (2×50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to give the target product Boc-L-glutamic acid-1-tert-butyl ester as a colorless oil. Yield: 25 g (92% yield, calculated based on Boc-Glu(OMe)-OH). The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3) and 13C NMR (75 MHz, CDCl3). | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 13, p. 3793 - 3797
[2] Journal of Organic Chemistry, 2005, vol. 70, # 22, p. 8730 - 8733
[3] Russian Chemical Bulletin, 2010, vol. 59, # 1, p. 110 - 115
[4] Journal of the American Chemical Society, 1993, vol. 115, # 15, p. 6646 - 6651
[5] Tetrahedron Letters, 2003, vol. 44, # 28, p. 5251 - 5253 |
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