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| | Boc-3-(2-Naphthyl)-L-alanine Basic information |
| | Boc-3-(2-Naphthyl)-L-alanine Chemical Properties |
| Melting point | 92-95 °C(lit.) | | Boiling point | 454.92°C (rough estimate) | | density | 1.2164 (rough estimate) | | refractive index | 1.5740 (estimate) | | storage temp. | Sealed in dry,Room Temperature | | solubility | soluble in Ethanol | | form | Solid | | pka | 3.88±0.30(Predicted) | | color | Off-white | | Optical Rotation | [α]20/D +45±2°, c = 1% in ethanol | | BRN | 4326467 | | Major Application | peptide synthesis | | InChI | 1S/C18H21NO4/c1-18(2,3)23-17(22)19-15(16(20)21)11-12-8-9-13-6-4-5-7-14(13)10-12/h4-10,15H,11H2,1-3H3,(H,19,22)(H,20,21)/t15-/m0/s1 | | InChIKey | URKWHOVNPHQQTM-HNNXBMFYSA-N | | SMILES | CC(C)(C)OC(=O)N[C@@H](Cc1ccc2ccccc2c1)C(O)=O | | CAS DataBase Reference | 58438-04-3(CAS DataBase Reference) |
| Hazard Codes | Xi | | Safety Statements | 22-24/25 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29225090 | | Storage Class | 11 - Combustible Solids |
| | Boc-3-(2-Naphthyl)-L-alanine Usage And Synthesis |
| Chemical Properties | beige to light brown powder | | Uses | N-Boc-3-(2-naphthyl)-L-alanine Functions as a reagent for the synthesis of dipeptidyl nitriles as potent and reversible inhibitors of Cathepsin C | | reaction suitability | reaction type: Boc solid-phase peptide synthesis | | Synthesis | The general procedure for the synthesis of 2-((tert-butoxycarbonyl)amino)-3-(naphthalen-2-yl)propanoic acid from the compound (CAS: 6960-34-5) and (E)-N-((tert-butoxycarbonyl)oxy)benzylidene cyanocyanide was as follows:
1. N-Butoxycarbonyl-L-3-(2-naphthalenyl)alanine (0.43 g, 2.0 mmol) was dissolved in a solvent mixture of dioxane (8 mL), water (8 mL) and triethylamine (4 mL).
2. BOC-ON (0.49 g, 2.0 mmol) was added and the reaction mixture was stirred overnight at room temperature under argon protection.
3. Upon completion of the reaction, the mixture was diluted with water (30 mL) and extracted with ethyl acetate (3 x 20 mL).
4. The aqueous layer was acidified to pH=4 with 10% citric acid solution and extracted with ethyl acetate (3 x 20 mL).
5. The organic phases were combined, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a colorless oily product (0.52 g, 82% yield).
6. The product was characterized by 1H NMR (DMSO-d6): δ 7.8 (3H, m), 7.7 (1H, s), 7.4 (3H, m), 7.15 (1H, d), 4.2 (1H, m), 3.2 (1H, m), 2.9 (1H, m), 1.3 (9H, s). | | References | [1] Patent: US5486597, 1996, A |
| | Boc-3-(2-Naphthyl)-L-alanine Preparation Products And Raw materials |
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