| Identification | More | [Name]
Boc-3-(2-Naphthyl)-L-alanine | [CAS]
58438-04-3 | [Synonyms]
BOC-2-L-NAPHTHYLALANINE
BOC-2-NAL-OH
BOC-3-(2-NAPHTHYL)-ALANINE
BOC-3-(2-NAPHTHYL)-L-ALANINE
BOC-ALA(2-NAPH)-OH
BOC-ALA(2-NAPHTHYL)-OH
BOC-ALA-BETA-(2-NAPHTHYL)-OH
BOC-BETA-(2-NAPHTHYL)-L-ALANINE
BOC-L-2-NAL-OH
BOC-L-2-NAPHTHYLALANINE
BOC-L-3-(2-NAPHTHYL)-ALANINE
BOC-NAL(2)-OH
N-ALPHA-T-BOC-BETA-(2-NAPHTHYL)-L-ALANINE
N-ALPHA-T-BUTOXYCARBONYL-3-(2-NAPHTHYL)-L-ALANINE
N-ALPHA-T-BUTOXYCARBONYL-L-3-(2-NAPHTHYL)-ALANINE
N-ALPHA-(TERT-BUTYLOXYCARBONYL)-3-(2-NAPHTHYL)-L-ALANINE
N-BOC-3-(2-NAPHTHYL)-L-ALANINE
N-TERT-BUTOXYCARBONYL-2-NAPHTHYL-L-ALANINE
N-(TERT-BUTOXYCARBONYL)-3-(2-NAPHTHYL)-L-ALANINE
RARECHEM BK PT 0098 | [Molecular Formula]
C18H21NO4 | [MDL Number]
MFCD00079671 | [Molecular Weight]
315.36 | [MOL File]
58438-04-3.mol |
| Chemical Properties | Back Directory | [Appearance]
beige to light brown powder | [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. ]
−20°C
| [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 | [CAS DataBase Reference]
58438-04-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29225090 |
| Hazard Information | Back Directory | [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 |
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