N-Boc-S-Trityl-L-cysteine Chemical Properties

Melting point:

143-146 °C(lit.)

alpha 

27.5 º (c=1, EtOH)

Boiling point:

610.9±55.0 °C(Predicted)

Density 

1.200±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

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

form 

Powder

pka

3.82±0.10(Predicted)

color 

White to off-white

optical activity

[α]20/D +27.5°, c = 1 in ethanol

BRN 

2028965

InChIKey

JDTOWOURWBDELG-QHCPKHFHSA-N

SMILES

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

CAS DataBase Reference

21947-98-8(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

F 

3-10

HS Code 

2930 90 16

MSDS

• Language:English Provider:SigmaAldrich

N-Boc-S-Trityl-L-cysteine Usage And Synthesis

Chemical Properties

White to yellow crystalline powder

Uses

Boc-Cys(Trt)-OH is used in method for preparing ularitide.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

General procedure for the synthesis of N-tert-butoxycarbonyl-S-trityl-L-cysteine from di-tert-butyl dicarbonate (Boc2O) and S-trityl-L-cysteine: S-trityl-L-cysteine (5 g, 12.7 mmol) was dissolved in 2N NaOH solution (80 mL), followed by the addition of di-tert-butyl dicarbonate (4.5 g, 20 mmol) . The reaction mixture was stirred at room temperature for 24 hours. After completion of the reaction, the aqueous solution was acidified to pH 2 with concentrated hydrochloric acid and then extracted with dichloromethane (2 x 100 mL). The organic phases were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the target compound N-tert-butoxycarbonyl-S-trityl-L-cysteine (5.3 g, 90% yield) as a white foamy solid without further purification.1H NMR (DMSO-d6) δ: 1.37 (s, 9H, tert-butyl-CH3); 2.29-2.58 (m , 2H, CH2); 3.76-3.79 (m, 1H, CH); 6.84 (d, J=7.8Hz, 1H, NH); 7.14-7.38 (m, 15H, triphenylmethyl-H).MALDI-TOF MS: m/z 464.8 [M+H]+, molecular weight 463.59 for calculated value C27H29NO4S.

References

[1] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 383 - 392
[2] Chemical Communications, 2013, vol. 49, # 92, p. 10808 - 10810
[3] Patent: CN106432014, 2017, A. Location in patent: Paragraph 0096; 0100; 0101; 0102; 0142; 0146; 0147; 0148
[4] Patent: WO2009/137251, 2009, A2. Location in patent: Page/Page column 30; 31
[5] Chemistry of Natural Compounds, 1979, vol. 15, p. 471 - 476

N-Boc-S-Trityl-L-cysteine(21947-98-8)Related Product Information

• Triphenylmethyl Chloride
• 1,1'-Carbonyldiimidazole
• Boc-S-(4-methylbenzyl)-L-cysteine
• N-Carbobenzyloxyglycine
• POLY(METHYLSILSESQUIOXANE)
• tert-Butyl carbazate
• tert-Butanol
• Trityl candesartan cilexetil
• L-Cysteine
• PENICILLIN V
• Carbonyl iron powder
• S-Trityl-L-cysteine
• Boc-S-trityl-D-cysteine
• BOC-S-TRITYL-D-CYSTEINE,N-ALPHA-T-BOC-S-TRITYL-D-CYSTEINE,BOC-D-TRITYL-L-CYSTEINE
• BOC-S-TRITYL-L-CYSTEINE N-HYDROXYSUCCINIMIDE ESTER
• BOC-PEN(TRT)-OH
• BOC-D-PEN(TRT)-OH
• N-Boc-S-Trityl-L-cysteine