CBZ-ALPHA-ALLYL-L-GLY Chemical Properties

storage temp. 

2-8°C

form 

Solid

color 

White to off-white

optical activity

Consistent with structure

CBZ-ALPHA-ALLYL-L-GLY Usage And Synthesis

Uses

(2S)-2-[[(phenylmethoxy)carbonyl]amino]-4-Pentenoic acid is a useful building block, and has been used in the regioselective preparation of nonracemic silylated amino acids.

Synthesis

(S)-(-)-2-Amino-4-pentenoic acid (2.0 g) was suspended in dioxane (80 mL) at room temperature and triethylamine (4.3 g), water (2.0 mL) and N-(phenylmethoxycarbonyloxy)succinimide (9.1 g) were added sequentially. The reaction mixture was stirred overnight at room temperature and then concentrated under vacuum. Subsequently, the reaction mixture was diluted with saturated NaHCO3 solution and extracted with ether (3 x 80 mL). The basic aqueous layer was acidified to pH 2 with 2N HCl and extracted with EtOAc (3 x 80 mL). The EtOAc layers were combined, washed with brine, dried over anhydrous Na2SO4, filtered and the solvent evaporated. Finally, a viscous oily product (4.41 g, quantitative yield) was obtained by concentration from toluene (2 × 20 mL). The product was confirmed by 1H NMR (300 MHz, DMSO-d6): δ 2.31-2.50 (m, 2H), 4.00-4.06 (m, 1H), 5.03 (s, 2H), 5.05-5.12 (m, 2H), 5.71-5.84 (m, 1H), 7.35 (m, 5H), 7.53 (d, 1H), 12.57 (bs, 1H). Mass spectrometry analysis (APCI) showed m/z = 250 ([M+H]+).LC/MS analysis (Method A) showed a retention time of 2.30 min.

References

[1] Patent: WO2004/80983, 2004, A1. Location in patent: Page 47
[2] Tetrahedron, 2013, vol. 69, # 30, p. 6275 - 6284
[3] Organic Letters, 2006, vol. 8, # 2, p. 239 - 242
[4] Patent: WO2011/15241, 2011, A1. Location in patent: Page/Page column 187; 398
[5] Patent: US2012/270881, 2012, A1. Location in patent: Page/Page column 116

CBZ-ALPHA-ALLYL-L-GLY(78553-51-2)Related Product Information

• METHYL-2-BOC-AMINO-4-PENTENOIC ACID
• L-Propargylglycine
• DL-PROPARGYLGLYCINE
• (S)-N-BOC-Propargylglycine
• (R)-METHYL-2-BOC-AMINO-4-PENTENOIC ACID
• DL-2-AMINO-4-PENTENOIC ACID
• 2-(Tert-Butoxycarbonylamino)Pent-4-Enoic Acid
• Boc-D-Allylglycine
• (S)-N-Boc-allylglycine
• (S)-Methyl-2-Boc-AMino-4-pentenoic acid
• D-Allylglycine
• CBZ-ALPHA-ALLYL-D-GLY
• L-Allylglycine
• CBZ-ALPHA-ALLYL-L-GLY
• CBZ-ALPHA-ALLYL-L-ALA