Identification | More | [Name]
Boc-Asp-OH | [CAS]
13726-67-5 | [Synonyms]
BOC-ASPARTIC ACID BOC-ASP-OH BOC-L-ASPARTIC ACID BOC-L-ASPARTIC ACID-OH BOC-L-ASP-OH N-ALPHA-T-BOC-L-ASPARTIC ACID N-ALPHA-T-BUTOXYCARBONYL-N-ASPARTIC ACID N-BOC-L-ASPARTIC ACID N-T-BUTOXYCARBONYL-L-ASPATIC ACID N-(TERT-BUTOXYCARBONYL)-L-ASPARTIC ACID N-TERT-BUTYLOXYCARBONYL-L-ASPARTIC ACID N-T-BOC-L-ASPARTIC ACID CRYSTALLINE BOC-L-Aspatic N-BOC-1-ASPARTICACID BOC-ASP BOC-L-ASPARTICACID(BOC-L-ASP-OH) Boc-L-Aspatic Acid BOC-L-ASP N-alpha-t-Butyloxycarbonyl-L-aspartic acid N-Boc-L-aspartic acid, 98+% | [EINECS(EC#)]
237-294-7 | [Molecular Formula]
C9H15NO6 | [MDL Number]
MFCD00037279 | [Molecular Weight]
233.22 | [MOL File]
13726-67-5.mol |
Chemical Properties | Back Directory | [Appearance]
white to off-white crystalline powder | [Melting point ]
116-118 °C(lit.)
| [alpha ]
-6 º (c=1, MeOH) | [Boiling point ]
375.46°C (rough estimate) | [density ]
1.3397 (rough estimate) | [refractive index ]
1.4640 (estimate) | [storage temp. ]
Store at RT. | [form ]
Crystalline Powder | [pka]
3.77±0.23(Predicted) | [color ]
White to off-white | [Optical Rotation]
[α]20/D 6.0°, c = 1 in methanol | [BRN ]
1913973 | [CAS DataBase Reference]
13726-67-5(CAS DataBase Reference) |
Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
29225090 |
Hazard Information | Back Directory | [Chemical Properties]
white to off-white crystalline powder | [Uses]
N-Boc-L-aspartic acid is an N-Boc-protected form of L-Aspartic acid (A790024). L-Aspartic acid is a nonessential amino acid that is used to biosynthesize other amino acids within the human body. L-Aspartic acid also increases membrane conductance of mammalian neurons by voltage-dependent means, causing depolarization and nerve impulses that travel to key areas of the central nervous system. | [Definition]
ChEBI: Nalpha-(tert-butoxycarbonyl)-l-aspartic acid is an aspartic acid derivative. | [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
GENERAL STEPS: In a 500 mL single-necked round-bottomed flask, L-aspartic acid (4 g, 30 mmol), 1,4-dioxane (120 mL) and deionized water (60 mL) were mixed to form a heterogeneous solution. Under continuous stirring, 1 M aqueous sodium hydroxide solution was added dropwise until the solution became homogeneous and clarified, indicating complete dissolution of L-aspartic acid. Subsequently, the reaction mixture was cooled in an ice bath and di-tert-butyl dicarbonate (7.2 g, 33 mmol) dissolved in 1,4-dioxane (20 mL) was added slowly and dropwise. The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, the solvent was partially evaporated using a rotary evaporator until the final volume was about 30 mL. ethyl acetate (20 mL) was then added and the aqueous layer was acidified to pH 2 with aqueous potassium bisulfate under ice-bath cooling conditions. the mixture was transferred to a partitioning funnel, and the product was extracted with ethyl acetate (3 aliquots at a time). The organic layers were combined and dried with anhydrous sodium sulfate. Subsequently, the solvent was evaporated using a rotary evaporator and further dried under vacuum overnight to give BOC-L-aspartic acid as a white solid (6 g, 85% yield).1H NMR (600 MHz, DMSO-d6) data: δ 1.38 (s, 9H), 2.51-2.55 (m, 1H), 2.65-2.69 (m, 1H). 4.24-4.28 (m, 1H), 7.05-7.07 (d, 1H, J = 12 Hz), 12.5 (s, 2H). | [References]
[1] Journal of the American Chemical Society, 2015, vol. 137, # 51, p. 16084 - 16097 [2] Patent: US2017/168042, 2017, A1. Location in patent: Paragraph 0203-0204 [3] Asian Journal of Chemistry, 2014, vol. 26, # 15, p. 4716 - 4722 [4] Patent: EP1647283, 2006, A1. Location in patent: Page/Page column 5 [5] Chemistry Letters, 1988, # 10, p. 1643 - 1646 |
|
|