ChemicalBook CAS DataBase List Boc-L-serine methyl ester

Boc-L-serine methyl ester synthesis

6synthesis methods

Product Name:Boc-L-serine methyl ester
CAS Number:2766-43-0
Molecular formula:C9H17NO5
Molecular Weight:219.24

24424-99-5

5680-80-8

2766-43-0

General procedure for the synthesis of Boc-L-serine methyl ester from di-tert-butyl dicarbonate and L-serine methyl ester hydrochloride: crude L-serine methyl ester hydrochloride (0.29 mol) was suspended in dichloromethane (200 mL), followed by the addition of triethylamine (79 mL, 0.57 mol) and di-tert-butyl dicarbonate (68 g, 0.31 mol) to the mixture. The reaction was carried out at 0°C. After removal of the cooling bath, the reaction mixture was stirred at room temperature overnight and then diluted with methyl tert-butyl ether (300 mL). The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by fast column chromatography on silica gel to afford Boc-L-serine methyl ester (60 g, 94% yield) as a colorless oil.

3262-72-4
407 suppliers
$10.00/1g

74-88-4
349 suppliers
$15.00/10g

2766-43-0
312 suppliers
$10.00/1g

Yield:2766-43-0 93%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 20; for 4.5 h;Cooling with ice;

Steps:

N-(tert-Butoxycarbonyl)-L-serine methyl ester (5)
To a solution of 4 (1.26 g, 6.1 mmol) and potassiumcarbonate (0.91 g, 6.6 mmol) in DMF (12 mL) cooled on an ice bath was added a solution of iodomethane (0.80mL, 12.8 mmol) in DMF (6 mL). After stirring for 30 min on an ice bath, the mixture was stirred for 4 h at rt.Precipitates were filtered off, and the filtrate was added with water and extracted with EtOAc. The organiclayer was washed with water and brine, dried over MgSO4, and evaporated. The obtained colorless oil waspurified by silica gel column chromatography (hexane:EtOAc = 1:1) to give 5 as a colorless oil (1.24 g, 93%).The spectral data of 5 were identical to the literature,25 and the purity was confirmed by 1H NMR.

References:

Shimodaira, Shingo;Iwaoka, Michio [Arkivoc,2016,vol. 2017,# 2,p. 260 - 271]

FullText

24424-99-5 Synthesis

24424-99-5
860 suppliers
$13.50/25G

5680-80-8 Synthesis

5680-80-8
463 suppliers
$10.00/5g

2766-43-0
312 suppliers
$10.00/1g

References

67-56-1 Synthesis