Methanol → HCID 86634302, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 2-tert-butoxycarbonylamino-5-(1-methyl-cyclopropyl)-thiazole-4-carboxylic acid (2 g, 6.7 mmol) in THF (100 mL) and cool to 0° C. under nitrogen. Add triethylamine (0.93 mL, 1 equiv.) followed by the dropwise addition of isobutyl chloroformate (0.87 mL, 1 equiv.). Stir 30 minutes at 0° C. then filter, washing with THF. Cool filtrate back to 0° C. then add sodium borohydride (0.76 g, 3 equiv.) in one sum followed by the dropwise addition of methanol (4.1 mL, 15 equiv.). After 45 minutes at 0° C. remove cooling bath and let warm to room temperature for 15 minutes. Quench reaction (cautiously) with 1 N HCl (aq), approximately 50 mL. Extract with DCM. Wash organics with aqueous saturated sodium chloride. Dry organics over MgSO4 then filter and concentrate. Purify on silica gel (2:1 Hexanes:Ethyl Acetate→1:1 Hexanes:Ethyl Acetate) to give a white solid (1.11 g, 58%). LCMS (ES), m/z 229 (M+1, product→t Butyl).

Provenance & Evidence