N-(tert-Butoxycarbonyl)-L-glutamine Chemical Properties

Melting point:

113-116 °C (dec.)(lit.)

alpha 

-3.5 º (c=2,C2H5OH)

Boiling point:

389.26°C (rough estimate)

Density 

1.2430 (rough estimate)

refractive index 

-4 ° (C=2, EtOH)

storage temp. 

Sealed in dry,2-8°C

solubility 

Soluble in DMSO and methanol. Soluble in 1 mmole in 2 ml DMF.

form 

Solid

pka

3.84±0.10(Predicted)

color 

White

optical activity

[α]20/D 3.5°, c = 1 in ethanol

BRN 

2127805

InChI

InChI=1S/C10H18N2O5/c1-10(2,3)17-9(16)12-6(8(14)15)4-5-7(11)13/h6H,4-5H2,1-3H3,(H2,11,13)(H,12,16)(H,14,15)/t6-/m0/s1

InChIKey

VVNYDCGZZSTUBC-LURJTMIESA-N

SMILES

C(O)(=O)[C@H](CCC(N)=O)NC(OC(C)(C)C)=O

CAS DataBase Reference

13726-85-7(CAS DataBase Reference)

EPA Substance Registry System

L-Glutamine, N2-[(1,1-dimethylethoxy)carbonyl]- (13726-85-7)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

TSCA 

TSCA listed

HS Code 

29241990

MSDS

• Language:English Provider:N-(tert-Butoxycarbonyl)-L-glutamine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

N-(tert-Butoxycarbonyl)-L-glutamine Usage And Synthesis

Chemical Properties

White fine crystalline powder

Uses

Protected Glutamine.

Uses

It is employed in the synthesis and analgesic activity of human .beta.-endorphin.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

Example 1: Synthesis of N-(Boc)-L-glutamine (1): L-glutamine (25 g, 0.17 mol) was dissolved in 300 mL of aqueous NaOH solution (21.9 g, 0.547 mol). The resulting solution was cooled to below 10 °C, followed by the slow addition of a THF (150 mL) solution of Boc anhydride (0.205 mol) (note that the reaction is exothermic). The reaction mixture was stirred continuously at 25 °C for 20 hours. The progress of the reaction was monitored by TLC and the unfolding agent was MeOH:CH2Cl2 (1:1, containing 0.1% AcOH). Upon completion of the reaction, the organic phase was separated and the aqueous phase was extracted with hexane (100 mL) and acidified to pH 2 with 2N HCl, followed by extraction with ethyl acetate (2 x 250 mL). The organic phases were combined, dried with Na2SO4 and the solvent was evaporated in vacuum. The resulting viscous oily product was diluted with dichloromethane and evaporated again. After standing for 2-3 days, it was crystallized from hexane to give N-(Boc)-L-glutamine (1) (37.5 g, 89% yield) as a colorless solid. The product was characterized by 1H NMR (DMSO, 300 MHz) and ESI-MS (m/z: 269 [M+Na]+).

References

[1] Journal of the American Chemical Society, 1997, vol. 119, # 17, p. 4086 - 4087
[2] Patent: WO2015/189856, 2015, A1. Location in patent: Page/Page column 14
[3] Synthetic Communications, 2008, vol. 38, # 2, p. 162 - 169
[4] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 8, p. 2777 - 2780
[5] Organic Syntheses, 1985, vol. 63, p. 160 - 160

N-(tert-Butoxycarbonyl)-L-glutamine(13726-85-7)Related Product Information

• BOC-L-Serine
• BOC-L-Asparagine
• Boc-D-Valine
• BOC-CYS-OH
• L-Glutamine
• Boc-L-Glutamic acid
• 4-BROMO-2,2-DIPHENYLBUTYRONITRILE
• 5-Methoxymethyl-2,3-pyridinedicarboxylic acid
• (2,3,4-trihydroxy-5-oxo-pentoxy)phosphonic acid
• BUTOXYCARBOXIM
• 1,3-dihydro-4-methyl-2H-1,5-benzodiazepin-2-one
• L-Glutamic acid, N-[4-[[(2,4-diamino-6-pteridinyl)methyl]formylamino]benzoyl]-, 1-(1,1-dimethylethyl) 5-methyl ester
• NALPHA-(TERT-BUTOXYCARBONYL)-D-GLUTAMINE,N-tert-Butoxycarbonyl-D-glutamine ,n(à)-tert-butoxycarbonyl-d-glutamine
• N-Boc-N'-(9-xanthenyl)-L-glutamine
• N-(tert-Butoxycarbonyl)-L-glutamine
• N-Boc-N'-trityl-L-glutamine
• NALPHA-tert-Butoxycarbonyl-L-glutamine 4-nitrophenyl ester
• BOC-N-GAMMA-ETHYL-L-GLUTAMINE