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151215-34-8

151215-34-8 Structure

151215-34-8 Structure
IdentificationBack Directory
[Name]

BOC-L-2-AMINO-4-BROMO-4-PENTENOIC ACID
[CAS]

151215-34-8
[Synonyms]

Boc-(S)-(2-bromoallyl)glycine
(S)-N-BOC-(2-BROMOALLYL)-GLYCINE
BOC-L-2-AMINO-4-BROMO-4-PENTENOIC ACID
BOC-L-2-AMINO-4-BROMO-4-PENTENOIC ACID USP/EP/BP
(S)-2-[(t-Butoxycarbonyl)amino]-4-bromo-4-pentenoic acid
(Tert-Butoxy)Carbonyl L-2-Amino-4-bromo-4-pentenoic acid
(S)-4-BroMo-2-((tert-butoxycarbonyl)aMino)pent-4-enoic acid
(2S)-4-bromo-2-{[(tert-butoxy)carbonyl]amino}pent-4-enoic acid
Boc-L-2-amino-4-bromo-4-pentenoic acid≥ 99% (HPLC, Chiral purity)
(2S)-4-bromo-2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-enoicaci
(2S)-4-bromo-2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-enoic acid
4-Pentenoic acid, 4-bromo-2-[[(1,1-dimethylethoxy)carbonyl]amino]-, (2S)-
[Molecular Formula]

C10H16BrNO4
[MDL Number]

MFCD01320852
[MOL File]

151215-34-8.mol
[Molecular Weight]

294.14
Chemical PropertiesBack Directory
[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)
Hazard InformationBack Directory
[Chemical Properties]

White crystalline powder
[Synthesis]

Di-tert-butyl dicarbonate

24424-99-5

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

151144-96-6

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

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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