(S)-(-)-ALPHA-AMINO-GAMMA-BUTYROLACTONE HYDROBROMIDE Chemical Properties

Melting point:

225 °C (dec.)(lit.)

storage temp. 

2-8°C

solubility 

Methanol (Slightly), Water (Slightly)

form 

Liquid

color 

Clear yellow to brownish, may darken on storage

optical activity

[α]20/D 21°, c = 1 in H2O

Sensitive 

Hygroscopic

BRN 

3912375

CAS DataBase Reference

15295-77-9(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

22-24/25-37/39-26

WGK Germany 

3

F 

3-10

HS Code 

29420000

MSDS

• Language:English Provider:SigmaAldrich

(S)-(-)-ALPHA-AMINO-GAMMA-BUTYROLACTONE HYDROBROMIDE Usage And Synthesis

Chemical Properties

WHITE TO SLIGHTLY YELLOW CRYSTALLINE POWDER

Uses

L-Homoserine Lactone Hydrobromide is a reactant in the synthesis of tritium labeled and photoactivatable N-acyl-L-homoserine lactones.

Uses

Used to prepare pseudopeptide inhibitors for Ras farnesyl-protein transferase as well as selenomethionine.

Synthesis

General procedure for the synthesis of α-amino-gamma-butyrolactone hydrobromide from L-methionine: Bromoacetic acid (46.0 kg), 2-propanol (69.0 kg), and acetic acid (69.0 kg) were sequentially added to an aqueous solution (69 kg) of L-methionine (46 kg) at ambient temperature. The resulting mixture was heated to reflux (85 °C to 95 °C) and stirred continuously at this temperature until the completion of the reaction was confirmed by 1H NMR. After completion of the reaction, the mixture was concentrated under reduced pressure and co-evaporated with 2-propanol. To the concentrated mixture was added 2-propanol (161.0 kg) followed by the slow addition of a 10 wt% HCl/dioxane solution (102 kg) at ambient temperature. The resulting slurry was heated to about 60°C and stirred for about 4 hours. Subsequently, the mixture was cooled to about 22°C and stirring was continued for about 2 hours. Filtration gave the product α-amino-γ-butyrolactone hydrobromide (Ma), which was was washed with two portions of 2-propanol (28 kg each) and dried under vacuum at 40 °C to give a white to off-white solid (39.3 kg, 70% yield).The 1H NMR (D2O) data were as follows: δ 4.79 (s, 2H), 4.61 (dd, 1H), 4.49-4.41 (m. 2H), 2.80 (m, 1H), 2.42 (m, 1H).

References

[1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 6, p. 938 - 954
[2] Organic and Biomolecular Chemistry, 2005, vol. 3, # 2, p. 253 - 262
[3] Molecules, 2013, vol. 18, # 3, p. 3266 - 3278
[4] Journal of the American Chemical Society, 2018, vol. 140, # 9, p. 3242 - 3249
[5] Patent: US2010/256366, 2010, A1. Location in patent: Page/Page column 20

(S)-(-)-ALPHA-AMINO-GAMMA-BUTYROLACTONE HYDROBROMIDE(15295-77-9)Related Product Information

• Gamma Butyrolactone
• Hydrogen bromide
• (-)-ALPHA-AMINO-GAMMA-BUTYROLACTONE HYDROBROMIDE,ALPHA-AMINO-GAMMA-BUTYROLACTONE HYDROBROMIDE,D,L-ALPHA-AMINO-GAMMA-BUTYROLACTONE HYDROBROMIDE
• (S)-(-)-ALPHA-AMINO-GAMMA-BUTYROLACTONE HYDROBROMIDE
• 3-FURANAMINE, TETRAHYDRO-
• (S)-3-AMINOTETRAHYDROFURAN
• 3-AMINODIHYDRO-2(3H)-FURANONE HYDROIODIDE
• L-Homoserine lactone hydrochloride
• L-HOMOSERINE LACTONE, HYDROCHLORIDE