Tert-butyl N-[2-(benzylaMino)ethyl]carbaMate

Tert-butyl N-[2-(benzylaMino)ethyl]carbaMate Property

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

Appearance

Colorless to light yellow Viscous Liquid

InChI

InChI=1S/C14H22N2O2/c1-14(2,3)18-13(17)16-10-9-15-11-12-7-5-4-6-8-12/h4-8,15H,9-11H2,1-3H3,(H,16,17)

InChIKey

ZSJCBAQDXIZTTC-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NCCNCC1=CC=CC=C1

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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.

P310Immediately call a POISON CENTER or doctor/physician.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

Tert-butyl N-[2-(benzylaMino)ethyl]carbaMate Chemical Properties,Usage,Production

Uses

tert-Butyl (2-(Benzylamino)ethyl)carbamate is used in preparation of AGC kinase inhibitor and application.

Synthesis

The general procedure for the synthesis of tert-butyl (2-(benzylamino)ethyl)carbamate from N-tert-butoxycarbonyl-1,2-ethylenediamine and benzaldehyde is as follows: 1. benzaldehyde (4.7 g, 44.0 mmol) was added to a methanol (60 mL) solution of N-Boc-1,2-ethylenediamine (6.4 g, 40.0 mmol). 2. The reaction mixture was stirred at room temperature overnight. 3. The reaction mixture was cooled to -10 °C (using an ice/salt bath) and NaBH4 (9.1 g, 240.0 mmol) was added in batches over 30 minutes. 4. After the addition was complete, the ice bath was removed and the reaction mixture was continued to be stirred at room temperature for 16 hours. 5. The solvent was evaporated and the residue was dissolved in EtOAc (150 mL) and poured into water (100 mL). 6. The organic layer was extracted with 0.5N HCl (3 x 100 mL). 7. The combined aqueous phases were cooled to 0°C and alkalized with saturated NaHCO3 solution. 8. The alkalized aqueous phase was extracted with CHCl3 (3 x 100 mL). 9. Combine the organic layers and wash with brine (200 mL). 10. Dry the organic layer with MgSO4, filter and evaporate the solvent in vacuum to obtain the target product tert-butyl (2-(benzylamino)ethyl)carbamate (9.2 g, 36.8 mmol, 92% yield) as a colorless oil. Product Characterization: - LC-MS [M + H]+: 251.2 (C14H22N2O2 + H, calculated value: 251.3). - TLC Rf (DCM/MeOH 9:1): 0.30.

References

[1] Patent: US2011/262355, 2011, A1. Location in patent: Page/Page column 135
[2] Patent: WO2011/133149, 2011, A1. Location in patent: Page/Page column 297-298
[3] Patent: WO2011/133150, 2011, A1. Location in patent: Page/Page column 299-300
[4] Patent: JP2016/41698, 2016, A. Location in patent: Paragraph 0364; 0375
[5] Chemical Communications, 2016, vol. 52, # 63, p. 9837 - 9840