L(+)-2-Amino-4-bromobutyric acid hydrobromide Chemical Properties

Melting point:

189 °C (dec.)(lit.)

alpha 

13 º (589nm, c=1, H2O)

refractive index 

17 ° (C=1, MeOH)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMF (Slightly), DMSO, Methanol (Slightly)

form 

Solid

color 

White to Light Brown

optical activity

[α]20/D +16°, c = 1 in methanol

Stability:

Unstable in Solution, Moisture Sensitive, Hygroscopic

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2922.49.8000

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

L(+)-2-Amino-4-bromobutyric acid hydrobromide Usage And Synthesis

Chemical Properties

white to light beige powder

Uses

(S)-(+)-2-Amino-4-bromobutyric acid hydrobromide may be used in the synthesis of metalloaminoacids such as [³⁴S]-enriched methionine (³⁴S-Met), telluromethionine (TeMet) and selenohomolanthionine (SeHLan).

Synthesis

The general procedure for the synthesis of L(+)-2-amino-4-bromobutyric acid hydrobromide from L-homoserine lactone hydrochloride is as follows: Example 14: Compound 322 ((2R,6S,13aS,14aR,16aS,Z)-6-(tert-butoxycarbonylamino)-14a-(2,5-dichlorothiophene-3-ylsulfonylcarbamoyl)-5,16-dioxo-2,3,5,6,7,8,10,11,13a,14,14a,15,16,16a-tetradecahydro- 1H-cyclopropan[e]pyrrolo[1,2:1,6,9]oxadiazole cyclopentadien-2-yl)4-chloroisoindole-2-carboxylate) was prepared as follows: Step 1: Synthesis of (-S)-2-amino-4-bromobutyric acid hydrobromide 3-Aminodihydrofuran-2(3H)-one hydrochloride (10.30 g, 74.87 mmol) was dissolved in 58 mL of a 30% w/w HBr solution of acetic acid and the reaction was stirred at 65 °C for 30 hrs. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The resulting solid was suspended in methyl tert-butyl ether (MTBE, 200 mL) and stirred for 30 minutes. The solid was collected by filtration, washed with MTBE (200 mL) and dried to give the target product (98% yield). Product characterization: 1H NMR (400 MHz, DMSO-d6) δ 8.37 (s, 3H), 4.01 (m, 1H), 3.65 (m, 2H), 2.33 (m, 2H).

References

[1] Journal of Medicinal Chemistry, 2014, vol. 57, # 5, p. 1753 - 1769
[2] Patent: WO2008/137779, 2008, A2. Location in patent: Page/Page column 158-160
[3] Organic Letters, 2008, vol. 10, # 24, p. 5521 - 5524
[4] Tetrahedron, 1985, vol. 41, # 10, p. 1833 - 1845
[5] Journal of Organic Chemistry, 2008, vol. 73, # 1, p. 168 - 176

L(+)-2-Amino-4-bromobutyric acid hydrobromide(15159-65-6)Related Product Information

• 4-Aminobutyric acid
• Eletriptan hydrobromide
• Glycine
• Scopolamine hydrobromide
• D-Glucosamine sulfate
• 6-Aminocaproic acid
• D-Glucosamine hydrochloride
• Barium sulfate
• FERRIC GLYCEROPHOSPHATE
• 4-AMINOAZOBENZENE HYDROCHLORIDE
• r-Amino Butryric Acid
• 4-Bromobutyric acid
• (S)-(+)-2-AMINO-4-BROMOBUTYRIC ACID METHYL ESTER
• 2-AMINO-4-BROMOBUTYRIC ACID HYDROBROMIDE
• (S)-2-AMINO-4-BROMOBUTANOIC ACID
• 2-AMINO-4-BROMOBUTANOIC ACID
• L(+)-2-Amino-4-bromobutyric acid hydrobromide
• DL-2,4-Diaminobutanoic acid