N-(tert-butoxycarbonyl)glycine → HCID 11854859, compound

Participants

Reaction Steps

A solution of 3-[4-(3-amino-2-hydroxy-propoxy)-3,5-dimethyl-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one (70 mg, 0.164 mmol, Example 99) in DCM (3 mL) is treated with DIPEA (85 mg, 0.655 mmol), TBTU (74 mg, 0.23 mmol) and tert. butoxycarbonyl glycine (43 mg, 0.246 mmol) and the reaction mixture is stirred at rt for 1 h. The mixture is diluted with EA and washed with sat. aq. NaHCO3 and brine. The organic extract is dried over MgSO4, filtered and evaporated. The residue is dissolved in DCM (2 mL) and TFA (0.1 mL) is added. The mixture is stirred at rt for 3 h before another portion of TFA (0.02 mL) is added. Stirring is continued for 1 h. The mixture is diluted with EA, washed twice with a sat. aq. NaHCO3 solution, dried over MgSO4, filtered and evaporated. The crude product is purified by chromatography on prep. TLC plates with DCM:methanol 9:1 to give 2-amino-N-(3-{2,6-dimethyl-4-[3-oxo-3-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propyl]-phenoxy}-2-hydroxy-propyl)-acetamide (3 mg) as a colourless resin; LC-MS: tR=0.86 min, [M+1]+=485.33.

Provenance & Evidence