Boc-3-(2-Naphthyl)-D-alanine Chemical Properties

Melting point:

92-95 °C(lit.)

alpha 

-45 º (c=1% in ethanol)

Boiling point:

454.92°C (rough estimate)

Density 

1.2164 (rough estimate)

refractive index 

1.5740 (estimate)

storage temp. 

Sealed in dry,2-8°C

solubility 

Chloroform (Sparingly), Ethanol (Sparingly), Methanol (Slightly)

form 

Solid

pka

3.88±0.30(Predicted)

color 

White

optical activity

[α]20/D 45±2°, c = 1% in ethanol

BRN 

4200660

CAS DataBase Reference

76985-10-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

22-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29242990

MSDS

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

Boc-3-(2-Naphthyl)-D-alanine Usage And Synthesis

Chemical Properties

off-white granular powder

Uses

Boc-3-(2-Naphthyl)-D-alanine is a reagent in Lanreotide trisulfide synthesis and somatostatin receptor binding activity. Reagent in the preparation by coupling and structure-activity relationships of arginine containing tripeptides as MC4 receptor ligands.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

1. N-tert-butoxycarbonyl-L-3-(2-naphthyl)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. After completion of the reaction, water (30 ml) was added for dilution and extracted with ethyl acetate (3 x 20 ml). 4. The aqueous layer was adjusted to pH=4 with 10% citric acid solution and extracted again 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 analyzed by 1H NMR. 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)-D-alanine(76985-10-9)Related Product Information

• D-Alanine
• Boc-3-(2-Naphthyl)-L-alanine
• EC 2.6.1.2
• Phenprobamate
• DL-Alanine
• Boc-beta-alanine
• β-Alanine
• 1-(1-NAPHTHYL)-2-THIOUREA
• L-Alanine
• DI-TERT-BUTYL ETHER
• BOC-L-4-Chlorophe
• BOC-L-2-Methylphe
• 5-Chloro-2-iodobenzoic acid
• BOC-L-3-THIENYLALANINE DCHA SALT
• BOC-D-4-Nitrophe
• Boc-L-serine methyl ester
• BOC-D-2-CYANOPHENYLALANINE
• BOC-D-SER-OME