| Identification | Back Directory | [Name]
L(+)-2-Amino-4-bromobutyric acid hydrobromide | [CAS]
15159-65-6 | [Synonyms]
Aminobromobutyricacidhydrobromide
L-2-AMINO-4-BROMOBUTYRIC ACID HBR
(2S)-2-amino-4-bromobutanoic acid
(S)-(+)-2-AMINO-4-BROMOBUTYRIC ACID HYD&
L(+)-2-AMINO-4-BROMOBUTYRIC ACID HYDROBROMIDE
(S)-2-AMino-4-broMobutanoic acid hydrobroMide
(S)-(+)-2-AMINO-4-BROMOBUTYRIC ACID HYDROBROMIDE
L(+)-2-Amino-4-bromobutyric acid hydrobromide,90%
(S)-(+)-2-Amino-4-bromobutyric acid hydrobromide 97%
(S)-(+)-2-AMINO-4-BROMOBUTYRIC ACID HYDROBROMIDE 98+% | [EINECS(EC#)]
2017-001-1 | [Molecular Formula]
C4H9Br2NO2 | [MDL Number]
MFCD01631290 | [MOL File]
15159-65-6.mol | [Molecular Weight]
262.93 |
| Chemical Properties | Back Directory | [Appearance]
white to light beige powder | [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 Rotation]
[α]20/D +16°, c = 1 in methanol | [Stability:]
Unstable in Solution, Moisture Sensitive, Hygroscopic |
| Hazard Information | Back Directory | [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 |
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