Welcome to chemicalbook!
Chinese English Japanese Germany Korea
010-86108875
Try our best to find the right business for you.
Do not miss inquiry messages Please log in to view all inquiry messages.

Welcome back!

ChemicalBook CAS DataBase List (S)-Methyl 2-((tert-butoxycarbonyl)aMino)-3-(3,4-dihydroxyphenyl)propanoate
37169-36-1

(S)-Methyl 2-((tert-butoxycarbonyl)aMino)-3-(3,4-dihydroxyphenyl)propanoate synthesis

6synthesis methods
Di-tert-butyl dicarbonate

24424-99-5

L-3,4-DIHYDROXYPHENYLALANINE METHYL ESTER HYDROCHLORIDE

1421-65-4

(S)-Methyl 2-((tert-butoxycarbonyl)aMino)-3-(3,4-dihydroxyphenyl)propanoate

37169-36-1

The general procedure for the synthesis of (S)-(2-((tert-butoxycarbonyl)amino)-3-(3,4-dihydroxyphenyl)propanoic acid methyl ester from di-tert-butyl dicarbonate and (S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid methyl ester hydrochloride was carried out as follows: under ice-bath conditions, a mixture of (S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid methyl ester hydrochloride (0.9 g 3.6 mmol) solution of THF (6.5 mL), saturated aqueous NaHCO3 solution (6.5 mL) and di-tert-butyl dicarbonate (0.87 g, 4.0 mmol) were added sequentially to the reaction flask. Subsequently, additional THF (4.0 mL) was added slowly. The reaction mixture was stirred at room temperature for 1 h, after which the organic solvent was removed by rotary evaporation. The aqueous phase was extracted three times with CH2Cl2 and the combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated to dryness. The residue was ground with Et2O and allowed to stand at low temperature. Finally, the target product (S)-(2-((tert-butoxycarbonyl)amino)-3-(3,4-dihydroxyphenyl)propanoic acid methyl ester was obtained by vacuum filtration.

-

Yield:-

Steps:

Multi-step reaction with 2 steps
1: thionyl chloride / 18 h / 20 °C
2: 11.320 g / NaHCO3 / tetrahydrofuran; H2O / 0 - 20 °C

References:

Tang, Shengzhuang;Martinez, Lynda J.;Sharma, Ajit;Chai, Minghui [Organic Letters,2006,vol. 8,# 20,p. 4421 - 4424]