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| | (S)-(-)-2-Methyl-2-propanesulfinamide Basic information | | Description |
| | (S)-(-)-2-Methyl-2-propanesulfinamide Chemical Properties |
| Melting point | 97-101 °C(lit.) | | alpha | -4.5 º (c=1, CHCl3) | | Boiling point | 220.0±23.0 °C(Predicted) | | density | 1.124 | | storage temp. | 2-8°C | | solubility | Chloroform (Slightly), Methanol (Slightly) | | pka | 10.11±0.50(Predicted) | | form | Crystalline Powder | | color | White | | Optical Rotation | [α]20/D 4.5°, c = 1 in chloroform | | Stability: | store cold | | InChI | InChI=1/C4H11NOS/c1-4(2,3)7(5)6/h5H2,1-3H3/t7-/s3 | | InChIKey | CESUXLKAADQNTB-SSDOTTSWSA-N | | SMILES | CC(C)([S@@](N)=O)C |&1:3,r| | | CAS DataBase Reference | 343338-28-3(CAS DataBase Reference) |
| | (S)-(-)-2-Methyl-2-propanesulfinamide Usage And Synthesis |
| Description | Acid labile protecting groups are important in organic synthesis. The
tert‐butyl group is commonly used for protection of a large variety of
functional groups, e.g., acids, alcohols, phenols, and sulfonamides.
Among them, s-tert-butyl sulfonamide is a chiral ligand used in
pharmaceutical compositions. P, n-sulfoxide imine ligands were
synthesized by condensation of s-tert-butylsulfonamide with aldehydes
and ketones, and they can be used for asymmetric hydrogenation of
olefins under iridium catalysis. | | Physical properties | white to light yellow crystal powder | | Uses | (S)-(-)-2-Methyl-2-propanesulfinamide is used in Suzuki reaction. It is also employed as a reagent for synthesizing chiral amines. It acts as a chiral auxiliary used in an asymmetric synthesis of trifluoroethylamines by conversion of trifluoroacetaldehyde to a chiral imine. It is also involved in the transformation of P,N-sulfinyl imine ligands through condensation with aldehydes and ketones, which can undergo iridium-catalyzed asymmetric hydrogenation of olefins. Further, it serves as a reagent for the preparation of chemicals and pharmaceutical intermediates. | | Uses | (S)-(-)-2-Methyl-2-propanesulfinamide may be used to develop benzofuran-based farnesyltransferase inhibitors as anti-cancer agents. It may also be used to prepare (20E)-N-[t-butyl-(S)-sulfinyl]-3β-(t-butyldimethylsilyloxy)-pregn-5-en-20-imine, an intermediate for the preparation of androgen receptor antagonists. | | Synthesis | The general procedure for the synthesis of S-tert-butylsulfinamide from (S)-tert-butylsulfinic acid thio-tert-butyl ester was as follows: in the third step, 120 mL of diethoxymethane was added to the reaction flask and the reaction temperature was controlled between -60 °C and -70 °C. Liquid ammonia (23.8 g, 1.40 mol) was slowly added dropwise to 2.6 mL of 2.3 M n-hexyl lithium (0.96 mol) solution, at which point a white solid gradually appeared in the solution. The reaction was maintained at this condition for 0.5 hr. Subsequently, a mixture of (S)-tert-butylsulfinyl tert-butyl thioester (169.8 g, 0.87 mol, 96.5% ee) and ethyl chloride (80.4 g, 1.25 mol) was added dropwise to the above mentioned diethoxymethane solution (which is the solution of the product obtained from the second step of the reaction) and cooled to 0 °C. After the dropwise addition was completed, the reaction was continued under stirring for 1 hour to ensure that the reaction was complete. Upon completion of the reaction, the reaction solution was concentrated to dryness under reduced pressure, 1400 mL of methyl tert-butyl ether was added, and the solvent was removed by filtration through diatomaceous earth and subsequent evaporation. The residue was slurried with 135 mL of n-heptane between -10 °C and 0 °C to afford fine needle-like crystals of S-tert-butylsulfinamide 79.1 g in 75% yield, 99.7% HPLC purity, and an enantiomeric excess value (ee) of 99.4%. | | References | [1] Patent: CN106478471, 2017, A. Location in patent: Paragraph 0018; 0019 |
| | (S)-(-)-2-Methyl-2-propanesulfinamide Preparation Products And Raw materials |
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