D-Homoserine, N-[(1,1-dimethylethoxy)carbonyl]- (9CI)

D-Homoserine, N-[(1,1-dimethylethoxy)carbonyl]- (9CI) Property

Boiling point:

421.6±40.0 °C(Predicted)

Density 

1.204±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

3.87±0.10(Predicted)

form 

solid

color 

White

optical activity

Consistent with structure

Safety

HS Code 

2924297099

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H332Harmful if inhaled

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

D-Homoserine, N-[(1,1-dimethylethoxy)carbonyl]- (9CI) Chemical Properties,Usage,Production

Uses

Boc-D-Homoserine is a serine derivative[1].

Synthesis

General procedure for the synthesis of (R)-2-((tert-butoxycarbonyl)amino)-4-hydroxybutyric acid from D-homoserine and di-tert-butyl dicarbonate: 1N NaOH (7.5 mL) was added to an ethanol-water (2:1, 21 mL) solution of D-homoserine (0.9 g, 7.5 mmol, 1 eq.), followed by di-tert-butyl dicarbonate (1.81 g, 8.3 mmol, 1.1 equiv) and THF (7 mL). The reaction mixture was stirred at room temperature for 16 hours. After the reaction was completed, the reaction mixture was extracted with diethyl ether (2 x 30 mL). The aqueous layer was cooled to 0 °C, acidified to pH 2 with 1N HCl and extracted with ethyl acetate (4 × 30 mL). The organic layers were combined and dried with Na2SO4. The solvent was concentrated under reduced pressure and the crude product was purified by column chromatography (cyclohexane/ethyl acetate, 1:1) to afford (R)-2-((tert-butoxycarbonyl)amino)-4-hydroxybutyric acid (3a) as a colorless oil. Yield: 1.35 g (6.1 mmol, 81%).1H NMR (300 MHz, D2O): δ = 1.38 (s, 9H, tert-butyl-CH3), 1.83-1.67 (m, 1H, 3-CH), 2.05-1.87 (m, 1H, 3-CH), 3.68-3.54 (m, 2H, 4-CH2), 3.97 ( dd, J = 4.7, 9.2 Hz, 1H, 2-CH).13C NMR (75 MHz, D2O): δ = 27.6 (tert-butyl-C), 33.8 (3-C), 52.7 (2-C), 58.3 (4-C), 81.0 (tert-butoxy-C), 157.6 (carbonyl-C), 179.0 (carboxy-C).HRMS ( ESI+, MeOH): m/z = 242.1002 [M + Na]+ (calculated value C9H17NO5Na+: 242.0999).

References

[1] Luckose F, et al. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144. DOI:10.1080/10408398.2012.708368