| Identification | More | [Name]
Boc-O-methyl-L-tyrosine | [CAS]
53267-93-9 | [Synonyms]
BOC-4-METHOXYPHENYLALANINE
BOC-4-METHOXY-PHE-OH
BOC-L-4-METHOXYPHE
BOC-L-TYR(ME)
BOC-L-TYR(ME)-OH
BOC-O-METHYL-L-TYROSINE
BOC-PHE(4-OME)-OH
BOC-P-METHOXY-PHE-OH
BOC-S-TYR(ME)-OH
BOC-TYR(ME)-OH
BOC-TYROSINE(ME)-OH
L-4'-METHOXY-N-BOC-TYROSINE
N-ALPHA-T-BOC-O-METHYL-L-TYROSINE
N-ALPHA-T-BOC-P-METHOXY-L-PHENYLALANINE
N-ALPHA-T-BUTOXYCARBONYL-4-METHOXY-L-PHENYLALANINE
N-ALPHA-T-BUTOXYCARBONYL-O-METHYL-L-TYROSINE
N-ALPHA-T-BUTOXYCARBONYL-O-METHY-L-TYROSINE
N-ALPHA-TERT-BUTYLOXYCARBONYL-O-METHYL-L-TYROSINE
(S)-2-TERT-BUTOXYCARBONYLAMINO-3-(4-METHOXY-PHENYL)-PROPIONIC ACID
(S)-N-ALPHA-T-BUTYLOXYCARBONYL-O-METHYL-TYROSINE | [Molecular Formula]
C15H21NO5 | [MDL Number]
MFCD00065603 | [Molecular Weight]
295.33 | [MOL File]
53267-93-9.mol |
| Chemical Properties | Back Directory | [Boiling point ]
462.0±40.0 °C(Predicted) | [density ]
1.168±0.06 g/cm3(Predicted) | [storage temp. ]
Store at 0-5°C | [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Solid | [pka]
3.00±0.10(Predicted) | [color ]
White to off-white | [Optical Rotation]
Consistent with structure | [Major Application]
peptide synthesis | [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) |
| Hazard Information | Back Directory | [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 |
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