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BOC-L-2-AMINO-4-BROMO-4-PENTENOIC ACID

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BOC-L-2-AMINO-4-BROMO-4-PENTENOIC ACID Basic information

Product Name:
BOC-L-2-AMINO-4-BROMO-4-PENTENOIC ACID
Synonyms:
  • (S)-N-BOC-(2-BROMOALLYL)-GLYCINE
  • BOC-L-2-AMINO-4-BROMO-4-PENTENOIC ACID
  • (2S)-4-bromo-2-{[(tert-butoxy)carbonyl]amino}pent-4-enoic acid
  • (2S)-4-bromo-2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-enoic acid
  • (S)-4-BroMo-2-((tert-butoxycarbonyl)aMino)pent-4-enoic acid
  • Boc-(S)-(2-bromoallyl)glycine
  • Boc-L-2-amino-4-bromo-4-pentenoic acid≥ 99% (HPLC, Chiral purity)
  • (Tert-Butoxy)Carbonyl L-2-Amino-4-bromo-4-pentenoic acid
CAS:
151215-34-8
MF:
C10H16BrNO4
MW:
294.14
Product Categories:
  • Unusual amino acids
Mol File:
151215-34-8.mol
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BOC-L-2-AMINO-4-BROMO-4-PENTENOIC ACID Chemical Properties

Boiling point:
396.7±42.0 °C(Predicted)
Density 
1.407±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
pka
3.81±0.10(Predicted)
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BOC-L-2-AMINO-4-BROMO-4-PENTENOIC ACID Usage And Synthesis

Chemical Properties

White crystalline powder

Synthesis

24424-99-5

151144-96-6

151215-34-8

4.3: After completion of the separation, the reaction mixture was extracted with ethyl acetate to remove the D-isomer to give L-2-amino-4-bromo-4-pentenoic acid. Subsequently, an aqueous solution of 5 L of acetone and 120 g of di-tert-butyl dicarbonate was added to the reaction system and the alkaline environment of the aqueous sodium carbonate solution was maintained. After the reaction was carried out for 5 hours, the reaction mixture was acidified with 3M hydrochloric acid and the product was extracted with ethyl acetate. The organic phase was dried and purified by crystallization to give 64 g of (S)-4-bromo-2-((tert-butoxycarbonyl)amino)pent-4-enoic acid as a solid. The purity of the product was 98.84% and the overall yield was 43.5% by HPLC analysis.

References

[1] Patent: CN107827767, 2018, A. Location in patent: Paragraph 0030; 0036
[2] Tetrahedron Letters, 1993, vol. 34, # 28, p. 4485 - 4488

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