Methyl N-(tert-butoxycarbonyl)-L-threoninate Chemical Properties

Boiling point:

206 °C(lit.)

Density 

1.123±0.06 g/cm3(Predicted)

refractive index 

n20/D 1.45(lit.)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Sparingly), Dichloromethane (Sparingly), DMF (Sparingly)

pka

11.00±0.46(Predicted)

form 

Viscous Liquid

color 

Yellow

Water Solubility 

Slightly soluble in water.

Safety Information

WGK Germany 

3

HS Code 

29241990

Methyl N-(tert-butoxycarbonyl)-L-threoninate Usage And Synthesis

Chemical Properties

Light yellow transparent oil

Uses

N-Boc-L-threonine methyl ester is used as pharmaceutical intermediates and chemical intermediate.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

The general procedure for the synthesis of Boc-D-alanine methyl ester from (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-hydroxybutanoic acid and dimethyl sulfate was as follows: 1) Synthesis of N-Boc-L-threonine methyl ester: Potassium carbonate (34.7 g, 250 mmol) and dimethyl sulfate (29.3 g, 232 mmol) were sequentially added to a solution of N-Boc-L-threonine (50.0 g, 213 mmol) in acetone (250 mL). The reaction mixture was heated to reflux for 1 h and subsequently cooled to room temperature in air. Insoluble solids were removed by filtration and the filtrate was concentrated under reduced pressure to remove the solvent to afford N-tert-butoxycarbonyl-L-threonine methyl ester as a colorless oil (54.6 g, 100% yield). The product was characterized by 1H-NMR (300 MHz, DMSO-d6): δ 1.26 (3H, d, J = 6.42 Hz), 1.46 (9H, s), 2.02 (1H, d, J = 5.14 Hz), 3.78 (3H, s), 4.28 (1H, m), 5.29 (1H, m). Mass spectra (FAB) showed molecular ion peak m/z: 234 ([M + H]+).

References

[1] Patent: EP1621537, 2006, A1. Location in patent: Page/Page column 25
[2] Patent: CN108003048, 2018, A. Location in patent: Paragraph 0013

Methyl N-(tert-butoxycarbonyl)-L-threoninate(79479-07-5)Related Product Information

• BOC-DL-PRO-OH
• N-Boc-4-oxo-L-Proline methyl ester
• BOC-TRP(BOC)-OH
• Boc-Tyr-OtBu
• Boc-D-Ser(tBu)-OH
• Boc-Hyp-OH
• 1-BOC-D-PYROGLUTAMIC ACID ETHYL ESTER
• Boc-D-Valine
• BOC-D-PHE-OSU
• Methyl dihydrojasmonate
• Methyl salicylate
• BOC-SER(TOS)-OCH3
• Boc-L-serine methyl ester
• BOC-GUANIDINE
• BOC-D-TYR(TBU)-OH
• Boc-L-Threonine
• BOC-L-THR(BZL)-O-CH2-PHI-CH2-COOH DCHA
• Methyl N-(tert-butoxycarbonyl)-L-threoninate