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| | TERT-BUTYL N-(BENZYLOXY)CARBAMATE Basic information |
| | TERT-BUTYL N-(BENZYLOXY)CARBAMATE Chemical Properties |
| 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 |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | HS Code | 29280000 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | TERT-BUTYL N-(BENZYLOXY)CARBAMATE Usage And Synthesis |
| 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 |
| | TERT-BUTYL N-(BENZYLOXY)CARBAMATE Preparation Products And Raw materials |
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