(2R,3S)-Methyl 2-hydroxy-3-(4-methylbenzenesulfonamido)-3-phenylpropanoate

Abstract

In the title mol­ecule, C17H19NO5S, the p-tolyl ring is oriented approximately parallel to the phenyl ring [dihedral angle = 17.2 (1)°], resulting in an intra­molecular π–π inter­ation [centroid–centroid distance = 3.184 (10) Å]. In the crystal, mol­ecules are linked through O—H⋯O and C—H⋯O hydrogen bonds, forming hydrogen-bonded sheets lying diagonally across the ac face.

tert-Butyl 2-hydroxy-3-(4-methylbenzenesulfonamido)butanoate

“…propanoate (Fadlalla et al, (2010). Other related structures have been reported by Coote et al (2008) and Liu et al, (2005).…”

“…For related structures of -amino alcohols, see: Lohray et al (2002); Bodkin et al (2008). For the structures of tosylamino compounds, see: Coote et al (2008); Liu et al (2005); Fadlalla et al (2010). For the synthesis of the title compound, see: Naicker et al (2008); Govender et al (2003).…”

Crystal structures of (RS)-N-[(1R,2S)-2-benzyloxy-1-(2,6-dimethylphenyl)propyl]-2-methylpropane-2-sulfinamide and (RS)-N-[(1S,2R)-2-benzyloxy-1-(2,4,6-trimethylphenyl)propyl]-2-methylpropane-2-sulfinamide: two related protected 1,2-amino alcohols

“…Although there are 78 structures of N-sulfinyl-protected 1,2amino alcohols in the Cambridge Structural Database (CSD, Version 5.35, last update May 2014;Groom & Allen, 2014), only seven of these structures have substitution at the 1-position and an aryl group at the 2-position. Of these compounds, only three have a tert-butanesulfinyl group [CSD refcodes CAVQOG (Zhong et al, 2005), FIZBIB (Jiang et al, 2014) and WOBNEI (Buesking & Ellman, 2014)], and the other four contain p-toluenesulfinyl groups [CSD refcodes PAQZIR (Zhao et al, 2005), RUXZUG (Ghorai et al, 2010), WADYOR (Fadlalla et al, 2010) and SICSII (Guo et al, 2012)]. However, none of these seven compounds were synthesized by our method of interest.…”