TERT-BUTYL N-(BENZYLOXY)CARBAMATE

TERT-BUTYL N-(BENZYLOXY)CARBAMATE Property

Melting point:

45-47 °C (lit.)

Density 

1.078±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Solid

color 

White

InChI

InChI=1S/C12H17NO3/c1-12(2,3)16-11(14)13-15-9-10-7-5-4-6-8-10/h4-8H,9H2,1-3H3,(H,13,14)

InChIKey

MZNBNPWFHGWAGH-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NOCC1=CC=CC=C1

CAS DataBase Reference

79722-21-7

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29280000

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.

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

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

TERT-BUTYL N-(BENZYLOXY)CARBAMATE Chemical Properties,Usage,Production

Chemical Properties

White powder

Uses

tert-Butyl N-(benzyloxy)carbamate was used in the preparation of seven-membered cyclic hydroxamic acids. It may be used in the synthesis of 2-(N-formyl-N-hydroxyamino) ethylphosphonate (IPP).

Uses

tert-Butyl N-(Benzyloxy)carbamate has been used in the synthesis of Deferoxamine Mesylate (D228980), an iron chelating agent used in therapy for patients with sickle cell diseases and iron overload. Studies suggest that it can exert potential antioxidant neuroprotective effects in stroke patients

General Description

tert-Butyl N-(benzyloxy)carbamate (tert-butyl benzyloxycarbamate), a protected hydroxylamine, is an N-alkyl-N-benzyloxy carbamate. Its C-N cross coupling reaction with fluorescein ditriflate has been reported. It participates in facile intramolecular cyclization with various carbon nucleophiles to afford functionalized 5- and 6-membered protected cyclic hydroxamic acids.

Synthesis

General procedure: synthesis of Intermediate 153: tert-butyl N-(benzyloxy)carbamate. To a solution of O-benzylhydroxylamine hydrochloride (225 g, 1.44 mol) in dichloromethane (300 mL) was added an aqueous sodium bicarbonate solution (261 g, 3.11 mol, 300 ml). After 1 hour of reaction, di-tert-butyl dicarbonate (375 g, 1.72 mol) was slowly added at 0°C. The reaction mixture was stirred in a water/ice bath at 0 °C for 60 min, followed by continued stirring for 16 h at room temperature. Upon completion of the reaction, the reaction was quenched by addition of 300 mL of aqueous sodium bicarbonate. The aqueous phase was separated and extracted with dichloromethane (3 x 500 mL), the organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by silica gel fast column chromatography (eluent: petroleum ether/ethyl acetate=10:1) afforded 220 g (69% yield) of the target compound, tert-butyl N-(benzyloxy)carbamate, as a yellow oil.1H NMR (300 MHz, CDCl3) δ: 1.43 (9H,s), 4.85 (2H,s), 7.19-7.21 (1H brs), 7.30-7.40 (5H, m).

References

[1] Journal of Organic Chemistry, 1997, vol. 62, # 26, p. 9148 - 9159
[2] Archiv der Pharmazie, 2016, vol. 349, # 5, p. 373 - 382
[3] Journal of Organic Chemistry, 1983, vol. 48, p. 24
[4] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 24, p. 8549 - 8555
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 19, p. 8847 - 8858