| Identification | More | [Name]
BOC-11-AMINOUNDECANOIC ACID | [CAS]
10436-25-6 | [Synonyms]
BOC-11-AUN-OH
BOC-NH-(CH2)10-COOH
Boc-11-aminoundecanoicaci
BOC-11-AMINOUNDECYLIC ACID
BOC-11-AMINOUNDECANOIC ACID
Boc-11-Aun-OH >=98.0% (TLC)
11-(BOC-AMINO)-UNDECANOIC ACID
N-ALPHA-T-BOC-11-AMINOUNDECANOIC ACID
REF DUPL: Boc-11-Aminoundecanoic acid
T-BUTOXYCARBONYL-11-AMINOUNDECYLIC ACID
10436-25-6 BOC-11-AMINOUNDECANOIC ACID
T-BUTOXYCARBONYL-11-AMINOUNDECANOIC ACID
N-T-BUTYLOXYCARBONYL-11-AMINO-UNDECANOIC ACID
N-(tert-Butoxycarbonyl)-11-aminoundecanoic acid
N-TERT-BUTYLOXYCARBONYL-11-AMINO-UNDECANOIC ACID
Boc-11-AMinoundecanoic acid Boc-11-AMinoundecanoic acid
11-[(2-methylpropan-2-yl)oxycarbonylamino]undecanoic acid
Undecanoic acid, 11-[[(1,1-dimethylethoxy)carbonyl]amino]- | [Molecular Formula]
C16H31NO4 | [MDL Number]
MFCD00076902 | [Molecular Weight]
301.42 | [MOL File]
10436-25-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
67-68 °C | [Boiling point ]
441.9±18.0 °C(Predicted) | [density ]
1.006±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
4.78±0.10(Predicted) | [color ]
White to Almost white | [BRN ]
1975656 | [InChI]
InChI=1S/C16H31NO4/c1-16(2,3)21-15(20)17-13-11-9-7-5-4-6-8-10-12-14(18)19/h4-13H2,1-3H3,(H,17,20)(H,18,19) | [InChIKey]
HPTPZJBSQUULAV-UHFFFAOYSA-N | [SMILES]
C(O)(=O)CCCCCCCCCCNC(OC(C)(C)C)=O | [CAS DataBase Reference]
10436-25-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HS Code ]
2924.19.8000 | [HazardClass ]
IRRITANT |
| Hazard Information | Back Directory | [Description]
Boc-11-aminoundecanoic acid is an alkane chain with terminal carboxlic acid and Boc-protected amino groups. The compound can be used as a PROTAC linker in the synthesis of PROTACs. 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]
White powder | [Uses]
Boc-11-aminoundecanoic acid is an Alkyl/ether-based?PROTAC linker?can be used in the synthesis of MS432 (HY-130602)[1]. | [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
General procedure for the synthesis of Boc-11-aminoundecanoic acid from 11-aminoundecanoic acid and di-tert-butyl dicarbonate: 160 g of 11-aminoundecanoic acid, 2 liters of dioxane, 1.3 liters of distilled water, 208 g of sodium carbonate, and 173 g of di-tert-butyl dicarbonate were added sequentially to a 4-liter three-necked flask in a unit equipped with a mechanical stirrer and reflux condenser. The reaction mixture was heated to boiling point and the reaction was continued with stirring for 16 hours to obtain a clarified solution. Upon completion of the reaction, the mixture was cooled to 20 °C and subsequently poured into 800 g of ice and the pH was adjusted to 3-4 with 4 N hydrochloric acid, at which point a white precipitate was produced. The precipitate was separated by filtration, washed with 300 cm3 of water and then dried under reduced pressure at 20 °C (20 mm Hg, 2.7 kPa) to give 232 g of N-(tert-butoxycarbonyl)-11-aminoundecanoic acid in 95% yield. The melting point of the product (68°C) is in agreement with that reported in the literature J. Org. Chem. 1997,1987.Chem., 41,1350 (1976). | [IC 50]
Alkyl/ether | [References]
[1] Wei J, et al.Discovery of a First-in-Class Mitogen-Activated Protein Kinase Kinase 1/2 Degrader.J Med Chem. 2019 Dec 12;62(23):10897-10911. DOI:10.1021/acs.jmedchem.9b01528 |
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