Home Cart Sign in  
Chemical Structure| 16874-12-7 Chemical Structure| 16874-12-7
Chemical Structure| 16874-12-7

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

H-Tyr-OtBu is a tyrosine derivative, commonly used in peptide synthesis and drug development.

Synonyms: (S)-2-Amino-3-(4-hydroxyphenyl)propionic acid tert-butyl ester; tert-Butyl(S)-2-amino-3-(4-hydroxyphenyl)propanoate; tert-Butyl L-tyrosinate

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of H-Tyr-OtBu

CAS No. :16874-12-7
Formula : C13H19NO3
M.W : 237.29
SMILES Code : [H][C@](N)(CC1=CC=C(O)C=C1)C(=O)OC(C)(C)C
Synonyms :
(S)-2-Amino-3-(4-hydroxyphenyl)propionic acid tert-butyl ester; tert-Butyl(S)-2-amino-3-(4-hydroxyphenyl)propanoate; tert-Butyl L-tyrosinate
MDL No. :MFCD00042644
InChI Key :DIGHFXIWRPMGSA-NSHDSACASA-N
Pubchem ID :6950582

Safety of H-Tyr-OtBu

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of H-Tyr-OtBu

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 16874-12-7 ]

[ 16874-12-7 ] Synthesis Path-Downstream   1~5

  • 2
  • [ 16874-12-7 ]
  • [ 63521-92-6 ]
  • Nα-pentenoyl-L-tyrosine tert-butyl ester [ No CAS ]
  • 3
  • [ 117-78-2 ]
  • [ 16874-12-7 ]
  • C28H25NO6 [ No CAS ]
  • 4
  • [ 24424-99-5 ]
  • [ 16874-12-7 ]
  • [ 18938-60-8 ]
YieldReaction ConditionsOperation in experiment
98% With triethylamine; In DMF (N,N-dimethyl-formamide); dichloromethane; at 20℃; for 2h; To a solution of 9.82 g (0.041 m) of (L)-tyrosine, tert-butyl ester in 150 ml of methylene chloride and 20 ml of DMF was added 5.2 g (0.04 m) of triethyl amine followed by 9.03 g (0.04 m) of ditertbutyldicarbonate. The reaction mixture was stirred for 2 hours at room temperature and was then washed with 1 N HCl (3×50 ml), NaHCO3 solution (1×50 ml) and brine (1×50 ml) and was dried over MgSO4. The mixture was filtered and concentrated in vacuo to give 13.59 g (98% yield) of a white solid. 300 MHz 1H NMR (CDCl3): 1.42 (s, 18H); 2.95 (d, 2H); 4.39 (dd, 1H); 5.01 (d, 1H); 6.15 (s, 1H); 6.70 (d, 2H); 7.00 d, 2H).
96% With triethylamine; In 1,4-dioxane; water; at 21℃;Inert atmosphere; To a stirred solution of Tyr-OBut (4) (5.0 g, 21.0 mmol) in dioxane and water (42 ml, 0.5 M, dioxane/water = 1/1) were added Et3N (3.27 g, 4.5 mL, 32.3 mmol, 1.54 equiv) and (Boc)2O (5.56 g, 24.4 mmol, 1.14 equiv). The reaction mixture was stirred at rt overnight. After confirming the completion of the reaction by TLC, the reaction mixture was acidified to pH 3 by adding 10% aqueous KHSO4, and extracted with EtOAc. The organic layers were washed with brine, dried (Na2SO4) and evaporated. Column chromatography on silica gel (petroleum ether/EtOAc = 20/1 then 2/1) to yield N-Boc-Tyr(OH)-OBut (5) (6.82 g, 96%) as a white solid, mp 106-107C (lit.12 112.8-113.0 C (nhexane/CH2Cl2)). The spectroscopic data of compound 5 were identical to those reported in the literature.
95% With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 20℃; for 3h; Example 1 (0506) This example details the synthesis of the carbonyl-containing amino acid presented in FIG. 4. The carbonyl-containing non-natural amino acid was produced as described in FIG. 4.
94% With sodium carbonate; In water; acetone; for 18h; To a stirring solution of sodium bicarbonate (37.4 g, 445 mmol) in water (1 L) was added (S)-tert-bity 2-amino-3-(4-hydroxyphenyl)propanoate (96 g, 405 mmol) and acetone (850 mL). A solution of di-tert-butyl dicarbonate (97 g, 445 mmol) in acetone (220 mL) was then added slowly over 2 h. After a further 16 h, the mixture was treated with water (1.7 L) then treated with a solution of AcOH (30 mL) in water (300 mL) added slowly. The mixture was extracted with EA (1 L) and the organics dried over Na2SO4 and partially concentrated. The residue was re-slurried with iso- hexanes (1 L). The precipitate was collected by filtration, washing with iso-hexanes (100 mL) to afford 128.4 g (94%) of tert-butyl (ri-butoxycarbonyl)-L-tyrosinate. LCMS-ESI (m/z) calculated for Ci8H27NO5: 337.2; found 360.2 [M+Na]+, tR = 5.93 min (Method 10).
85% With triethylamine; In 1,4-dioxane; water; at 20℃; To a solution of commercially available L-tyrosine ieri-butyl ester (700 mg, 2.95 mmol) in 50 mL of Dioxane-H20 (5: 1), NEt3 (1.23 ml, 8.85 mmol) and (Boc)20 (966 mg, 4.42 mmol) were added, and the reaction mixture was stirred at room temperature. When TLC indicated the consumption of L- tyrosine ieri-butyl ester, the reaction mixture was concentrated under reduced pressure to remove dioxane, and then the resulting solution was diluted with water and extracted with EtOAc (2 chi 50 mL). The combined organic layer was washed with brine, dried over Na2S04, filtered, and concentrated under reduced pressure to give the crude product. Purification by flash chromatography on silica gel with MeOH:CH2CI2 (1 :20) afforded the title compound as a white solid (846 mg, 85%). For more details and analytical data, see: Wang, L; Qu, W.; Lieberman, B. P.; Plossl, K.; Kung, H. F. Nucl. Med. Biol. 201 1, 38, 53-62)
77% With triethylamine; In dichloromethane; at 0 - 20℃; for 18h; Step 1. 2-Methyl-2-propanyl N-[(2-methyl-2-propanyl)oxy]carbonyl}-L-tyrosinate To a solution of L-tyrosine tert-butyl ester (1.43 g, 2.64 mmol) in CH2Cl2 (5.0 mL) was added triethylamine (0.320 mL, 2.31 mmol) and di-tert-butyldicarbonate (0.303 g, 1.39 mmol) at 0 C. After the solution was stirred at room temperature for 18 h, the solution was diluted with CH2Cl2 and washed with 2 N HCl(aq). The organic layer was dried over MgSO4(s), filtered, and concentrated. The residue was purified by Isco Combi-Flash Companion column chromatography (0-30% ethyl acetate in n-hexane) to give 2-methyl-2-propanyl N-[(2-methyl-2-propanyl)oxy]carbonyl}-L-tyrosinate (299 mg, 77%) as a white solid. 1H NMR (CDCl3, 400 MHz) delta 7.02 (d, 2H), 6.73 (d, 2H), 5.59 (br s, 1H), 5.00 (br d, 1H), 4.39 (q, 1H), 3.01-2.92 (m, 2H), 1.42 (s, 9H), 1.41 (s, 9H).
With triethylamine; In dichloromethane; at 0 - 20℃;Inert atmosphere; INTERMEDIATE 4fert-Butyl (2^)-2-r(fer?-butoxycarbonyl)amino]-3-(4-hvdroxyphenyl)propanoate; A solution of di-fert-butyl dicarbonate (6.81 g, 31.2 mmol) in dry CH2Cl2 (15 mL) was added dropwise via cannula to a stirred solution of L-tyrosine tert-butyl ester (6.17 g, 26.0 mmol) and triethylamine (5.26 g, 7.25 mL, 52.0 mmol) al 0 0C under N2. The reaction was stirred at room temperature overnight. Water (30 mL) was added and the mixture was stirred for 30 min. The organic layer was washed with water (20 mL), 0.05 M HCl (20 mL), water (20 mL) and brine (20 mL), dried (MgSO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Biotage Horizon, 65i, Si, ~70 mL/min, 100% hexanes for 450 mL, gradient to 25% EtOAc in hexanes over 4446 mL, gradient to 40% EtOAc in hexanes over 2448 mL) to afford tert-bxxty (2S)-2-[(ferr-butoxycarbonyl)amino]-3-(4- hydroxyrhohenyl)propanoate. R/ = 0.28 (20% EtOAc/hexanes). LCMS calc, = 360.2; found = 359,9 (M+Na)+. 1H NMR (500 MHz, CDCl3): delta 7.02 (d, J= 8.1 Hz, 2 H); 6.73 (d, J = 8.1 Hz, 2 H); 5.41 (s, I H); 4.99 (d, J= 7.9 Hz, 1 H); 4.40 (q, J- 6.6 Hz, 1 H); 3.01-2.93 (m, 2 H); 1.42 (s, 9 H); 1.41 (s, 9 H).

  • 5
  • [ 16874-12-7 ]
  • [ 28697-11-2 ]
  • [ 875151-92-1 ]
YieldReaction ConditionsOperation in experiment
97% 24a)(S)-2-[(S)-l -tert-Butoxycarbonyl-2-(4-hydroxy-phenyl)-ethylcarbamoyl] -piperidine-1 -carboxylic acid benzyl ester; 2-lH-Benzotriazol-l-yl-l5l,3,3-tetramethyluroniumtetrafluoroborate (TBTU, 4.15 g, 12.9mmoles) was added to a room temperature solution of (S)-2-amino-3-(4-hydroxy-phenyl)-propionic acid tert-butyl ester (1.70 g, 7.17 mmoles) and 1-methylimidazole (2.60 mL, 32.7mmoles) in 1,2-DCE (15 mL). After stirring at room temperature for 20 min, a solution of(S)-piperidine-l,2-dicarboxylic acid 1-benzyl ester (1.70 g, 6.46 mmoles) in 1,2-DCE (15 mL)was added, and the resulting mixture was stirred at room temperature for 48 h. The reactionmixture was diluted with EtOAc (200 mL) and washed with brine (3x200 mL). The aqueouslayers were re-extracted with EtOAc (2x200 mL). The organic layers were dried (Na2SO4),combined, and concentrated in vacuo to give 4.21 g of an oil. Purification of the residue byflash chromatography on silica gel, eluting with 0-20% EtOAc/CH2Cl2 afforded 3.02 g (97%yield) of the title compound as a light yellow oil.
97% 2-1H-Benzotriazol-1-yl-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU, 4.15 g, 12.9 mmoles) was added to a room temperature solution of (S)-2-amino-3-(4-hydroxy-phenyl)-propionic acid tert-butyl ester (1.70 g, 7.17 mmoles) and 1-methylimidazole (2.60 mL, 32.7 mmoles) in 1,2-DCE (15 mL). After stirring at room temperature for 20 min, a solution of (S)-piperidine-1,2-dicarboxylic acid 1-benzyl ester (1.70 g, 6.46 mmoles) in 1,2-DCE (15 mL) was added, and the resulting mixture was stirred at room temperature for 48 h. The reaction mixture was diluted with EtOAc (200 mL) and washed with brine (3×200 mL). The aqueous layers were re-extracted with EtOAc (2×200 mL). The organic layers were dried (Na2SO4), combined, and concentrated in vacuo to give 4.21 g of an oil. Purification of the residue by flash chromatography on silica gel, eluting with 0-20% EtOAc/CH2Cl2 afforded 3.02 g (97% yield) of the title compound as a light yellow oil.
 

Historical Records

Categories