| Identification | More | [Name]
Boc-3-(2-Naphthyl)-D-alanine | [CAS]
76985-10-9 | [Synonyms]
BOC-2-L-NAPHTHYLALANINE
BOC-2-NAL-OH
BOC-3-(2-NAPHTHYL)-ALANINE
BOC-3-(2-NAPHTHYL)-D-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)-D-ALANINE
BOC-BETA-(2-NAPHTHYL)-L-ALANINE
BOC-D-2-NAL-OH
BOC-D-2-NAPHTHYLALANINE
BOC-D-3-(2-NAPHTHYL)-ALANINE
BOC-D-ALA(2-NAPH)-OH
BOC-D-ALA(2-NAPHTHYL)-OH
BOC-D-ALA-BETA-(2-NAPHTHYL)-OH
BOC-D-NAL(2)-OH
BOC-L-2-NAL-OH
BOC-L-2-NAPHTHYLALANINE
BOC-L-3-(2-NAPHTHYL)-ALANINE | [Molecular Formula]
C18H21NO4 | [MDL Number]
MFCD00079671 | [Molecular Weight]
315.36 | [MOL File]
76985-10-9.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white granular powder | [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. ]
−20°C
| [solubility ]
Chloroform (Sparingly), Ethanol (Sparingly), Methanol (Slightly) | [form ]
Solid | [pka]
3.88±0.30(Predicted) | [color ]
White | [Optical Rotation]
[α]20/D 45±2°, c = 1% in ethanol | [BRN ]
4200660 | [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-/m1/s1 | [InChIKey]
URKWHOVNPHQQTM-OAHLLOKOSA-N | [SMILES]
CC(C)(C)OC(=O)N[C@H](Cc1ccc2ccccc2c1)C(O)=O | [CAS DataBase Reference]
76985-10-9(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 ]
29242990 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [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 |
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