1-(Tert-butoxycarbonyl)-3-(methanesulfonyloxy)azetidine Chemical Properties

Melting point:

69 °C

Boiling point:

378.5±31.0 °C(Predicted)

Density 

1.28±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

-4.18±0.40(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C9H17NO5S/c1-9(2,3)14-8(11)10-5-7(6-10)15-16(4,12)13/h7H,5-6H2,1-4H3

InChIKey

XXBDTKYKFFIAEY-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CC(OS(C)(=O)=O)C1

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN 2811 6.1 / PGIII

HazardClass 

IRRITANT

HS Code 

2933998090

1-(Tert-butoxycarbonyl)-3-(methanesulfonyloxy)azetidine Usage And Synthesis

Synthesis

Preparation of Example 26-2: tert-butyl 3-((methylsulfonyl)oxy)azetidine-1-carboxylate Under a nitrogen atmosphere, methanesulfonyl chloride (2.57 mL, 33.3 mmol) and triethylamine (11.6 mL, 83.1 mmol) were sequentially added to a solution of tetrahydrofuran (100 mL) containing N-Boc-3-hydroxyazetidine (4.8 g, 27.7 mmol). The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, saturated aqueous sodium bicarbonate solution was added to the reaction solution and the mixture was diluted with ethyl acetate. The organic layer was separated, washed with saturated brine and subsequently dried over anhydrous sodium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under vacuum. The residue was purified by silica gel column chromatography (eluent ratio: n-heptane/ethyl acetate = 9:1 to 1:1) to quantitatively obtain N-Boc-3-methylsulfonyloxyazetidine. 1H-NMR (CDCl3) δ (ppm): 1.45 (9H, s), 3.07 (3H, s), 4.03-4.18 (2H, m), 4.22-4.36 (2H, m), 5.12-5.27 (1H, m).

References

[1] Patent: US2014/235614, 2014, A1. Location in patent: Paragraph 0570; 0571; 0572
[2] Patent: EP1340757, 2003, A1
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 18, p. 7731 - 7757
[4] Patent: WO2018/102419, 2018, A1. Location in patent: Paragraph 0344; 0345; 0346; 0347
[5] Patent: US2012/10182, 2012, A1. Location in patent: Page/Page column 40

1-(Tert-butoxycarbonyl)-3-(methanesulfonyloxy)azetidine(141699-58-3)Related Product Information

• 3-[(TERT-BUTOXYCARBONYL)AMINO]ETHYL METHANESULFONATE
• 1-(Tert-butoxycarbonyl)-3-(methanesulfonyloxy)azetidine
• 1-BOC-3-(TOLUENE-4-SULFONYLOXY)-AZETIDINE
• 1-N-Boc-3-hydroxyazetidine