BOC-SER(ME)-OH Chemical Properties

Boiling point:

355.8±37.0 °C(Predicted)

Density 

1.148±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

form 

solid

pka

3.52±0.10(Predicted)

color 

Yellow-brown

InChI

InChI=1S/C9H17NO5/c1-9(2,3)15-8(13)10-6(5-14-4)7(11)12/h6H,5H2,1-4H3,(H,10,13)(H,11,12)/t6-/m0/s1

InChIKey

RFGMSGRWQUMJIR-LURJTMIESA-N

SMILES

C(O)(=O)[C@H](COC)NC(OC(C)(C)C)=O

CAS DataBase Reference

51293-47-1(CAS DataBase Reference)

Safety Information

HazardClass 

IRRITANT

HS Code 

2924297099

BOC-SER(ME)-OH Usage And Synthesis

Chemical Properties

White to off-white crystals

Uses

BOC-SER(ME)-OH, also known as Boc-Ser-OMe or N-tert-butyloxycarbonyl-L-serine methyl ester, is an amino acid derivative commonly used in peptide synthesis.

Synthesis

General procedure for the synthesis of N-Boc-O-methyl-L-serine from O-methyl DL-serine and di-tert-butyl dicarbonate: 35 mL of aqueous 1 N sodium hydroxide solution and 35 mL of tetrahydrofuran (THF) were added to 2.0 g (17 mmol) of O-methyl DL-serine. With stirring at 0 °C, a solution of di-tert-butyl dicarbonate (4.03 g, 18.5 mmol) in THF (15 mL) was added slowly. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the reaction mixture was concentrated by evaporation under reduced pressure. The aqueous phase was acidified to pH 4-5 with 10% aqueous citric acid and then extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give 3.6 g of N-Boc-O-methyl-L-serine (98% yield). Mass spectrum (ESI) m/z: 220.1 (M + H)+.

References

[1] Chemistry - A European Journal, 2011, vol. 17, # 15, p. 4183 - 4194
[2] Patent: WO2016/11088, 2016, A2. Location in patent: Paragraph 00238; 00239

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