| Identification | Back Directory | [Name]
BENZYL 3-OXOCYCLOBUTYLCARBAMATE | [CAS]
130369-36-7 | [Synonyms]
3-(Cbz-amino)cyclobutanone
3-Z-amino-cyclobutanone, 98%
BENZYL 3-OXOCYCLOBUTYLCARBAMATE
benzyl N-(3-oxocyclobutyl)carbamate
Phenylmethyl N-(3-oxocyclobutyl)carbamate
3-Aminocyclobutanone, N-CBZ protected 97%
(3-Oxo-cyclobutyl)-carbamic acid benzyl ester
N-(Benzyloxycarbonyl)-3-amino-1-cyclobutanone
(3-Oxocyclobutyl)carbamic acid phenylmethyl ester
Carbamic acid, N-(3-oxocyclobutyl)-, phenylmethyl ester | [EINECS(EC#)]
1533716-785-6 | [Molecular Formula]
C12H13NO3 | [MDL Number]
MFCD13152267 | [MOL File]
130369-36-7.mol | [Molecular Weight]
219.239 |
| Chemical Properties | Back Directory | [Boiling point ]
403.3±44.0 °C(Predicted) | [density ]
1.22 | [storage temp. ]
2-8°C | [pka]
11.39±0.20(Predicted) | [Appearance]
Off-white to yellow Solid | [InChI]
InChI=1S/C12H13NO3/c14-11-6-10(7-11)13-12(15)16-8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,13,15) | [InChIKey]
PSAMWNBBHLUISE-UHFFFAOYSA-N | [SMILES]
C(OCC1=CC=CC=C1)(=O)NC1CC(=O)C1 |
| Hazard Information | Back Directory | [Uses]
Benzyl 3-Oxocyclobutylcarbamate is used in process for preparation of abrocitinib. | [Synthesis]
3-Oxocyclobutanecarboxylic acid (1.0 g, 8.77 mmol) and benzyl alcohol (1.14 g, 10.52 mmol) were used as raw materials, and 3-oxocyclobutanecarboxylic acid was mixed with DIEA (1.92 g, 14.92 mmol) and DPPA (2.89 g, 10.52 mmol) in toluene (8 mL) under argon protection. The reaction mixture was heated to 60 °C and maintained for 3 h. Benzyl alcohol was then added. Stirring was continued at 60 °C overnight. Upon completion of the reaction, the reaction mixture was concentrated and the residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate = 8:1) to afford the target product benzyl 3-oxocyclobutylcarbamate (240 mg, 50% yield). The product was characterized by 1H NMR (500 MHz, CDCl3) and ESI-MS: 1H NMR δ 7.38-7.33 (m, 5H), 5.12 (d, J = 7.5 Hz, 2H), 4.34-4.33 (brs, 1H), 3.44-3.39 (m, 2H), 3.10-3.07 (brs, 2H) ppm; ESI-MS (m/z): 220.2 [M + 1]+. | [References]
[1] Patent: WO2012/75381, 2012, A1. Location in patent: Page/Page column 210
[2] Patent: WO2012/9678, 2012, A1. Location in patent: Page/Page column 210
[3] Patent: EP1256578, 2002, A1. Location in patent: Page 22
[4] Patent: WO2014/74421, 2014, A1. Location in patent: Page/Page column 56; 57 |
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