Boc-Tyr(Me)-OH Chemical Properties

Boiling point:

462.0±40.0 °C(Predicted)

Density 

1.168±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

pka

3.00±0.10(Predicted)

form 

Solid

color 

White to off-white

optical activity

Consistent with structure

InChI

InChI=1S/C15H21NO5/c1-15(2,3)21-14(19)16-12(13(17)18)9-10-5-7-11(20-4)8-6-10/h5-8,12H,9H2,1-4H3,(H,16,19)(H,17,18)/t12-/m0/s1

InChIKey

SLWWWZWJISHVOU-LBPRGKRZSA-N

SMILES

C(O)(=O)[C@H](CC1=CC=C(OC)C=C1)NC(OC(C)(C)C)=O

CAS DataBase Reference

53267-93-9(CAS DataBase Reference)

Safety Information

WGK Germany 

3

HS Code 

2924 29 70

HazardClass 

IRRITANT

MSDS

• Language:English Provider:SigmaAldrich

Boc-Tyr(Me)-OH Usage And Synthesis

Chemical Properties

White powder

Uses

Boc-Tyr(Me)-OH, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

Application

Boc-Tyr(Me)-OH, also known as N-Boc-O-methyl-L-tyrosine, is used to incorporate O-methyltyrosine, a structural component of many potent vasopressin antagonists and oxytocin antagonists.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

To a solution of methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-methoxyphenyl)propionate (498 mg, 1.61 mmol) in THF/MeOH/H2O (3:1:1, 5 mL) was added LiOH-H2O (142 mg, 3.22 mmol) at 0 °C. The reaction mixture was stirred at 0 °C for 1 h and then evaporated to remove the organic solvent. The residue was treated with 15% aqueous citric acid solution, adjusting the pH to 3, and subsequently extracted with ethyl acetate (35 mL). The combined organic layers were washed with brine (5 mL), dried over anhydrous Na2SO4 and concentrated in vacuum. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate/petroleum ether=2:1) to afford (S)-2-((tert-butoxycarbonyl)amino)-3-(4-methoxyphenyl)propanoic acid (466 mg, 98%) as a colorless oil.1H NMR (300 MHz, CD3OD): δ 7.13 (2H, d, J=8.4 Hz), 6.82 (2H d, J=8.4 Hz), 4.31-4.29 (1H, m), 3.73 (3H, s), 3.08 (1H, dd, J=13.8, 4.5 Hz), 2.85 (1H, dd, J=13.5, 8.7 Hz), 1.38 (9H, s).13C NMR (75 MHz, CD3OD): δ 175.42, 159.95, 157.00, 159.95, 157.00 (9H, s). 159.95, 157.67, 131.27, 130.37, 114.81, 80.50, 56.37, 55.64, 37.86, 28.67.

References

[1] Tetrahedron, 2014, vol. 70, # 37, p. 6630 - 6640
[2] Patent: CN107353239, 2017, A. Location in patent: Paragraph 0173; 0174
[3] Patent: CN107468690, 2017, A. Location in patent: Paragraph 0173; 0174
[4] Synthesis, 1984, vol. NO. 7, p. 572 - 574
[5] Journal of Organic Chemistry, 1981, vol. 46, # 9, p. 1944 - 1946

Boc-Tyr(Me)-OH(53267-93-9)Related Product Information

• N-(tert-Butoxycarbonyl)-L-phenylalanine
• 6-Aminocaproic acid
• 4-Nitro-3-phenyl-L-alanine
• H-ARG-ARG-LEU-ILE-GLU-ASP-ASN-GLU-TYR-THR-ALA-ARG-GLY-OH
• Glycine
• N-Carbobenzyloxyglycine
• Boc-D-Tyr-OH
• tert-Butanol
• Methylparaben
• Methyl acrylate
• Bensulfuron methyl
• Kresoxim-methyl
• BOC-L-Tyrosine
• Phenprobamate
• L-Tyrosine
• Boc-Aib-OH
• L-Phenylalanine
• Boc-2-Methyl-D-beta-phenylalanine