BOC-GLU-OME Chemical Properties

Melting point:

119-123℃

Boiling point:

428.4±40.0 °C(Predicted)

Density 

1.182±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

4.48±0.10(Predicted)

color 

Off-White to Light Yellow

InChI

InChI=1S/C11H19NO6/c1-11(2,3)18-10(16)12-7(9(15)17-4)5-6-8(13)14/h7H,5-6H2,1-4H3,(H,12,16)(H,13,14)/t7-/m0/s1

InChIKey

ZAYAFKXUQMTLPL-ZETCQYMHSA-N

SMILES

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

BOC-GLU-OME Usage And Synthesis

Chemical Properties

White to off-white crystalline powder

Uses

N-Boc-L-glutamic Acid α-Methyl Ester is a glutamate derivative that undergoes vitamin K-dependent carboxylation in liver microsomes.

Synthesis

The general procedure for the synthesis of (S)-4-((tert-butoxycarbonyl)amino)-5-methoxy-5-oxopentanoic acid from methyl (S)-5-benzyl-2-((tert-butoxycarbonyl)amino)pentanedioate was as follows: methyl (S)-5-benzyl-2-((tert-butoxycarbonyl)amino)pentanedioate (4.95 g, 14.09 mmol) was dissolved in 50 mL of a round bottom flask of methanol (20 mL) and 10% palladium/carbon catalyst was added under nitrogen protection. Subsequently, the reaction vessel was purged three times with nitrogen and hydrogen alternately. The reaction mixture was stirred for 6 hours under hydrogen atmosphere and atmospheric pressure. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated to afford the target compound (S)-4-((tert-butoxycarbonyl)amino)-5-methoxy-5-oxopentanoic acid as a colorless gelatinous liquid (3.5 g, 96% yield). The specific optical rotation of the product [α]21D = +7 (c 0.1, CHCl3). Nuclear magnetic resonance hydrogen spectrum (1H NMR, CDCl3, 400 MHz) δ: 1.4 (s, 9H), 1.87-1.96 (m, 1H), 2.12-2.15 (m, 1H), 2.35-2.49 (m, 2H), 3.71 (s, 3H), 4.31-4.33 (d, 1H, J = 4.64 Hz), 5.24- 5.27 (d, 1H, J = 8.16 Hz), 10.19 (s, 1H). Nuclear magnetic resonance carbon spectrum (13C NMR, CDCl3, 100 MHz) δ: 27.5, 28.2, 30.0, 52.4, 52.8, 80.2, 155.5, 172.8, 177.7. infrared spectrum (IR, KBr) νmax: 3346, 2979, 1719, 1520, 1439, 1394, 1369. 1216, 1167, 1057, 1029, 879, 853, 816, 780, 596, 463 cm-1.

References

[1] Tetrahedron Letters, 1998, vol. 39, # 15, p. 2099 - 2102
[2] Organic and Biomolecular Chemistry, 2007, vol. 5, # 9, p. 1459 - 1465
[3] Chemical Communications, 2005, # 37, p. 4652 - 4654
[4] Tetrahedron Letters, 2014, vol. 55, # 14, p. 2274 - 2276
[5] Heterocycles, 2015, vol. 90, # 2, p. 1309 - 1316

BOC-GLU-OME(72086-72-7)Related Product Information

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• BOC-GLU(OSU)-OBZL
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• BOC-GLU(OSU)-OTBU
• BOC-GLU(OTBU)-OBZL
• BOC-L-GLUTAMIC ACID DIBENZYL ESTER
• Boc-Glu-OCHEX
• BOC-L-GLU(OCHX)-O-CH2-PHI-CH2-COOH
• BOC-GLU(OTBU)-ONP
• BOC-GLU-PHENYL ESTER