Triphenylphosphine → tert-butyl (S)-1-((S)-5-((1-ethyl-1H-indol-4-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate

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Reaction Steps

DEAD 40% w/w (359 mg, 376 μl, 826 μmol, Eq: 3) was added to a mixture of tert-butyl methyl((S)-1-oxo-1-((S)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)propan-2-yl)carbamate (100 mg, 275 μmol, Eq: 1.00), (1-ethyl-1H-indol-4-yl)methanol (48.2 mg, 275 μmol, Eq: 1.00) and polymer-bound Ph3P (500 mg, 275 μmol, Eq: 1.00) in THF (10 mL). After 2.5 d., additional portions of (1-ethyl-1H-indol-4-yl)methanol (48.2 mg, 275 μmol, Eq: 1.00), polymer-bound Ph3P (1 eq) and DEAD (1 eq), were added. After 1 d, the mixture was filtered and the filter cake washed with MeOH and THF. The filtrate was concentrated and the residue was purified by preparative TLC to afford tert-butyl (S)-1-((S)-5-((l-ethyl-1H-indol-4-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (73 mg, 51%).

Provenance & Evidence