BENZYL N-(2-HYDROXYETHYL)CARBAMATE

BENZYL N-(2-HYDROXYETHYL)CARBAMATE Property

Melting point:

58-60 °C (lit.)

Boiling point:

215 °C/15 mmHg (lit.)

Density 

1.1926 (rough estimate)

refractive index 

1.5150 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in water or 1% acetic acid

pka

11.80±0.46(Predicted)

form 

Powder

color 

White

BRN 

2050891

InChI

InChI=1S/C10H13NO3/c12-7-6-11-10(13)14-8-9-4-2-1-3-5-9/h1-5,12H,6-8H2,(H,11,13)

InChIKey

SAGINAGERRNGGV-UHFFFAOYSA-N

SMILES

C(OCC1=CC=CC=C1)(=O)NCCO

CAS DataBase Reference

77987-49-6(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29221985

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

BENZYL N-(2-HYDROXYETHYL)CARBAMATE Chemical Properties,Usage,Production

Chemical Properties

White powder

Uses

N-(Benzyloxycarbonyl)ethanolamine is an intermediate used to prepare alkynylaryladenines as A2A adenosine receptor agonists and effects on hepatic glucose production. It is also used in the synthesis of functionalized N-arylaminoethyl amides as noncovalent inhibitors of cathepsin S.

reaction suitability

reagent type: cross-linking reagent

Synthesis

(1) Synthesis of benzyl [2-(tert-butyldiphenylmethoxysilyl)ethyl]carbamate [1515]: To a solution of 2-aminoethanol (2.0 g, 32.7 mmol) in dichloromethane (60 mL), benzyl chloroformate (5.6 mL, 41.3 mmol) and triethylamine (5.5 mL, 39.5 mmol) were sequentially added under ice bath conditions. The reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with the eluent being toluene:acetonitrile (3:2) to afford benzyl (2-hydroxyethyl)carbamate (5.37 g, 84% yield) as a white solid. [1516] Subsequently, to a solution of benzyl (2-hydroxyethyl)carbamate (5.37 g, 27.5 mmol) in dimethylformamide (160 mL) was added tert-butyldiphenylmethylsilyl chloride (8.6 mL, 33.0 mmol) and imidazole (2.3 g, 33.8 mmol) under ice bath conditions. The mixture was stirred at room temperature overnight. After the reaction was complete, ethanol was added and stirring was continued for 2 hours. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with hexane:ethyl acetate (5:1) as eluent to give benzyl [2-(tert-butyldiphenylmethylsilylmethoxy)ethyl]carbamate (11.93 g, 100% yield) as a colorless transparent syrup. [1517] 1H-NMR (400 MHz, CDCl3): δ (ppm) 7.64 (4H, d, J = 6.8 Hz), 7.46-7.28 (12H, m), 5.10 (2H, s), 3.73 (2H, t, J = 4.9 Hz), 3.35 (2H, q, J = 4.9 Hz), 1.05 (9H, s).

References

[1] Patent: US2004/14962, 2004, A1. Location in patent: Page/Page column 137
[2] Journal of Organic Chemistry, 1987, vol. 52, # 7, p. 1252 - 1255
[3] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 15, p. 1749 - 1750
[4] Tetrahedron Letters, 2007, vol. 48, # 46, p. 8170 - 8173
[5] Tetrahedron, 1991, vol. 47, # 14/15, p. 2591 - 2602