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| | tert-Butyl (Mesitylsulfonyl)oxycarbaMate Basic information |
| Product Name: | tert-Butyl (Mesitylsulfonyl)oxycarbaMate | | Synonyms: | Benzenesulfonic acid,2,4,6-triMethyl-, [(1,1-diMethylethoxy)carbonyl]azanyl ester;1,1-dimethylethyl [[(2,4,6-trimethylphenyl)sulphonyl]oxy]carbamate;N-[[(2,4,6-Trimethylphenyl)sulfonyl]oxy]carbamic acid tert-butyl ester;N-Tert-butoxycarbonyl-O-(mesitylsulfonyl)hydroxylamine;N-BOC-O-(MESITYLSULFONYL)HYDROXYLAMINE;N-Mesitylsulfonyloxy-tert-butylcarbaMat;N-Boc-O-(mesitylsulfonyl)hydroxyamine;[(2-methylpropan-2-yl)oxycarbonylamino] 2,4,6-trimethylbenzenesulfonate | | CAS: | 36016-39-4 | | MF: | C14H21NO5S | | MW: | 315.39 | | EINECS: | 252-837-8 | | Product Categories: | | | Mol File: | 36016-39-4.mol |  |
| | tert-Butyl (Mesitylsulfonyl)oxycarbaMate Chemical Properties |
| Melting point | 104-105.5 °C | | density | 1.191±0.06 g/cm3(Predicted) | | storage temp. | Hygroscopic, Refrigerator, under inert atmosphere | | solubility | DMSO (Slightly), Methanol (Slightly) | | form | Solid | | color | White to Off-White | | Stability: | Hygroscopic | | InChI | InChI=1S/C14H21NO5S/c1-9-7-10(2)12(11(3)8-9)21(17,18)20-15-13(16)19-14(4,5)6/h7-8H,1-6H3,(H,15,16) | | InChIKey | WVMDSNGINQNHLN-UHFFFAOYSA-N | | SMILES | C1(S(ONC(OC(C)(C)C)=O)(=O)=O)=C(C)C=C(C)C=C1C |
| | tert-Butyl (Mesitylsulfonyl)oxycarbaMate Usage And Synthesis |
| Uses | Tert-Butyl (Mesitylsulfonyl)oxycarbaMate is a useful reagent for the enantioselective aziridination of α,β-unsaturated aldehydes. | | Synthesis | 
2-Mesitylenesufonylchloride (2.00 g, 9.17 mmol) was added to a flame dried and argon purged round-bottom flask and dissolved in ether (18 mL), followed by the addition of N-Boc-hydroxylamine (1.47 g, 1100 mmol) The flask was cooled to 0° C and then TEA was added dropwise (1.3 mL). The reaction stirred for 2 hours at 0° C, at which all starting material had been converted as seen by TLC. The TEA-Cl, white solid, was filtered, and washed with ether. The filtrate was concentrated in vacuo, and purified via flash chromatography in 25/75 EtOAc/hexane gradient. Yield was quantitative, 2.16 g, white solid. | | Purification Methods | Separation of 1,1-Dimethylethyl (((2,4,6-trimethylphenyl)sulphonyl)oxy)carbamate on Newcrom R1 HPLC column:1,1-Dimethylethyl (((2,4,6-trimethylphenyl)sulphonyl)oxy)carbamate can be analyzed by this reverse phase (RP) HPLC method with simple conditions. The mobile phase contains an acetonitrile (MeCN), water, and phosphoric acid. For Mass-Spec (MS) compatible applications the phosphoric acid needs to be replaced with formic acid. Smaller 3 μm particles columns available for fast UPLC applications. This liquid chromatography method is scalable and can be used for isolation impurities in preparative separation. It also suitable for pharmacokinetics. |
| | tert-Butyl (Mesitylsulfonyl)oxycarbaMate Preparation Products And Raw materials |
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