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 activity

[α]20/D +45±2°, c = 1% in ethanol

BRN 

4326467

CAS DataBase Reference

58438-04-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

22-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29225090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

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(58438-04-3)Related Product Information

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• N-Carbobenzyloxyglycine
• D-Alanine
• EC 2.6.1.2
• L-Alanine
• 1-(1-NAPHTHYL)-2-THIOUREA
• tert-Butanol
• Boc-3-(2-Naphthyl)-D-alanine
• BOC-BETA-(1-NAPHTHYL)-L-ALANINE,N-ALPHA-T-BOC-BETA-(1-NAPHTHYL)-L-ALANINE,BOC-3-(1-NAPHTHYL)-L-ALANINE
• BOC-3-(1-NAPHTHYL)-D-ALANINE,BOC-BETA-(1-NAPHTHYL)-D-ALANINE,N-ALPHA-T-BOC-BETA-(1-NAPHTHYL)-D-ALANINE
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• 3-(2-Naphthyl)-L-alanine
• 3-(2-NAPHTHYL)-L-ALANINE HYDROCHLORIDE
• BOC-3-(2-NAPHTHYL)-L-ALANINE MERRIFIELD RESIN
• D-BOC-3-(2-NAPHTHYL)-BETA-ALANINE
• BOC-3-(1-PYRENYL)-L-ALANINE
• L-Alanine
• BOC-(S)-ALPHA-(2-NAPHTHALENYLMETHYL)-PROLINE