(1S)-(+)-Camphor-10-sulphonic acid → HCID 86636752, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-7-(2-(2-fluoro-5-((4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethylamino)-1-hydroxyethyl)-4-hydroxybenzo[d]thiazol-2(3H)-one (4.3 g, 6.42 mmol) (example 47A), (1S)-(+)-10-camphorsulfonic acid (2.98 g, 12.84 mmol) and iso-propanol (300 mL) was heated at 50° C. until a clear solution formed, seeded, allowed to cool to RT and stirred for 4 days. The solid was isolated by filtration, washed with iso-propanol (100 mL), ether (2×200 mL) and sucked dry to give the titled compound as a white crystalline solid. Yield 5.1 g The enantiomeric excess of the title compound is higher than the compound obtained in example 47A. (example 47A=86% ee, title compound >96% ee)

Provenance & Evidence