(S)-5-Chloro-3-{[2-(phenoxymethyl)morpholin-4-yl]sulfonyl}-1H-indole-2-carboxamide → Ethyl (S)-5-chloro-3-{[2-(phenoxymethyl)morpholin-4-yl]sulfonyl}-1-(phenylsulfonyl)-1H-indole-2-carboxylate

Participants

Reaction Steps

The product from Step A of Example 22 was resolved by preparative chiral HPLC (ChiralPak AD) to produce a first-eluting enantiomer and a second-eluting enantiomer. To assign the (S)-configuration to the first-eluting enantiomer, (S)-2-(phenoxymethyl)morpholine (from resolution of the racemate by preparative ChiralPak AD HPLC) was converted to the titled product using the procedure described in Step A of Example 22. The configuration of (S)-2-(phenoxymethyl)morpholine was assigned by 1H NMR analysis of the derived Mosher's amide (cf. J. Org. Chem. 1996, 61, 2056-2064).

Provenance & Evidence