Chloroacetyl chloride → HCID 87546119, compound

Participants

Reaction Steps

To a solution of EXAMPLE 208B (187 mg, 0.44 mmol) in H2O (2 mL)/THF (1 mL) was chloroacetyl chloride (110 mg, 0.97 mmol) in THF (3 mL) dropwise added under a period of 40 min. The temperature was kept at 8° C. and 2 M KOH was added continuously to adjust the pH to around 6-8. Aqueous potassium hydroxide (6 M, 0.38 mL, 1.41 mmol) was added and the mixture was stirred at room temperature for 20 min. The pH was adjusted to 8 and the mixture was extracted with ethyl acetate. The organic phase was separated and the solvent was evaporated. The residue was flash chromatographed on silica gel eluting with 30% acetone in DCM, yielding 98 mg (52 %) of the title compound: MS (Ionspray, [M+H]+) m/z 429. Anal. Calcd. (found) for C17H20ClN3O4S2: C, 47.5 (47.4)%; H, 4.7 (4.9)%; N, 9.8 (9.5)%.

Provenance & Evidence