Reacción #67573

Ecuación de reacción

DIAD

triphenylphosphine

5-(3,3-dimethyl-but-1-ynyl)-3-[(3-hydroxy-1-(S)-methyl-propyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid TFA salt

phthalimide

→

5-(3,3-Dimethyl-but-1-ynyl)-3-[[3-(1,3-dioxo-1,3-dihydro-isoindole-2-yl)-1-(S)-methyl propyl]-(trans-4-methyl-cyclohexylcarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester

Rendimiento 92.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   TemperaturaAfter warming to rt
3. 3
   OtroThe reaction was quenched with CH3OH (1.0 mL)
4. 4
   Otrothe solvent removed under reduced pressure

Procedimiento

A mixture of 5-(3,3-dimethyl-but-1-ynyl)-3-[(3-hydroxy-1-(S)-methyl-propyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid TFA salt (1.40 g, 3.23 mmol) in THF (30 mL) was cooled to 0° C. and triphenylphosphine (2.53 g, 9.69 mmol) was added followed by phthalimide (0.713 g, 4.84 mmol). The reaction was stirred until homogenious then DIAD (1.06 mL, 5.49 mmol) was added. After warming to rt., the reaction was determined to be complete by LC/MS in 1 h. The reaction was quenched with CH3OH (1.0 mL) and the solvent removed under reduced pressure. 5-(3,3-Dimethyl-but-1-ynyl)-3-[[3-(1,3-dioxo-1,3-dihydro-isoindole-2-yl)-1-(S)-methyl propyl]-(trans-4-methyl-cyclohexylcarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (1.67 g, 92%) was isolated by silica gel chromatography as an off-white solid.

Fuente