| Identification | More | [Name]
Boc-5-aminopentanoic acid | [CAS]
27219-07-4 | [Synonyms]
5-(BOC-AMINO)PENTANOIC ACID
5-(BOC-AMINO)VALERIC ACID
5-(TERT-BUTOXYCARBONYLAMINO)PENTANOIC ACID
5-(TERT-BUTOXYCARBONYLAMINO)VALERIC ACID
BOC-5-AMINOPENTANOIC ACID
BOC-5-AMINOVALERIC ACID
BOC-5-AVA-OH
BOC-APE(5)-OH
BOC-DELTA-AMINOVALERIC ACID
BOC-NH-(CH2)4-COOH
N-BOC-5-AMINOPENTANOIC ACID
N-BOC-5-AMINOVALERIC ACID
N-DELTA-T-BUTOXYCARBONYL-DELTA-AMINOVALERIC ACID
N-T-BUTOXYCARBONYL-5-AMINOPENTANOIC ACID
PENTANOIC ACID, 5-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-
RARECHEM EM WB 0073
5-(Boc-amino)pentanoic acid, 5-(Boc-amino)valeric acid
5-[(tert-Butyloxycarbonyl)amino]pentanoic acid
5-[[(1,1-Dimethylethyl)oxy]carbonyl]aminopentanoic acid | [Molecular Formula]
C10H19NO4 | [MDL Number]
MFCD00076903 | [Molecular Weight]
217.26 | [MOL File]
27219-07-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
48-52 °C(lit.) | [Boiling point ]
160-168 °C0.8 mm Hg(lit.) | [density ]
1.1518 (rough estimate) | [refractive index ]
1.4500 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [solubility ]
soluble in Methanol | [form ]
Powder | [pka]
4.72±0.10(Predicted) | [color ]
Off-white | [BRN ]
2048862 | [CAS DataBase Reference]
27219-07-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
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
| [F ]
10-21 | [HazardClass ]
IRRITANT | [HS Code ]
29241990 |
| Hazard Information | Back Directory | [Description]
Boc-5-aminopentanoic acid can be used as a PROTAC linker in the synthesis of PROTACs. Boc-5-aminopentanoic acid is an alkane chain with terminal carboxlic acid and Boc-protected amino groups. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond. The Boc group can be deprotected under mild acidic conditions to form the free amine. | [Chemical Properties]
solid | [Uses]
Boc-5-aminovaleric acid can be used to synthesize inhibitors of bacterial quorum seining and biofilm formation. It can also be used to synthesize diblock and triblock copolymers. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 48, p. 2424, 1983 DOI: 10.1021/jo00162a028 | [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
Example 4: To a mixed solution of 100 mL of 2% aqueous sodium hydroxide and 100 mL of dioxane containing 5-aminopentanoic acid (5.85 g, 0.05 mol), a solution of dioxane containing di-tert-butyl dicarbonate (10.9 g, 0.05 mol) was slowly added dropwise. The reaction mixture was stirred at room temperature for 18 h and then acidified with 1 N hydrochloric acid to pH 3. The acidified reaction mixture was extracted three times with dichloromethane. The organic layers were combined, washed sequentially with water and dried over sodium sulfate, and concentrated under reduced pressure to give 10.1 g (93.5% yield) of 5-(tert-butoxycarbonylamino)pentanoic acid as a white crystalline solid. | [References]
[1] Journal of the American Chemical Society, 2018, vol. 140, # 44, p. 14599 - 14603
[2] ChemMedChem, 2016, p. 1172 - 1187
[3] ChemMedChem, 2016, vol. 11, # 11, p. 1172 - 1187
[4] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 4, p. 402 - 407
[5] Patent: US4476228, 1984, A |
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