Trifluoroacetic acid → Ethyl acetate methanol ammonium hydroxide

N-(Triphenylmethyl)-O-[4-[6-benzyloxy-3-[3-methoxy-4-[(1-pyrrolidinyl)methyl]benzyl]benzo[b]thiophen-2-yl]phenyl]-L-serine methyl ester (165 mg, 0.18 mmol) in dichloromethane (5 mL) was treated with triethylsilane (0.3 mL) and trifluoroacetic acid (0.3 mL) at ambient temperature for 30 min. The solvent and excess reagents were removed under reduced pressure. The residue was dissolved in THF (3 mL) and treated with an aqueous solution of ammonium formate (25%, 2 mL) and palladium on carbon (10%, 50 mg) at ambient temperature for 21 h before filtration through diatomaceous earth with dichloromethane and methanol rinse. The filtrate was extracted with dichloromethane (30 mL×3) which was washed with water (50 mL). The combined organic layers were dried with sodium sulfate and concentrated under reduced pressure. Chromatography with NH4OH:MeOH:EtOAc (3:7:90) afforded the product as a white solid (26 mg, 25%).

1. customThe solvent and excess reagents were removed under reduced pressure
2. dissolutionThe residue was dissolved in THF (3 mL)
3. additiontreated with an aqueous solution of ammonium formate (25%, 2 mL) and palladium on carbon (10%, 50 mg) at ambient temperature for 21 h before filtration through diatomaceous earth with dichloromethane and methanol
4. washrinse
5. extractionThe filtrate was extracted with dichloromethane (30 mL×3) which
6. washwas washed with water (50 mL)
7. dry with materialThe combined organic layers were dried with sodium sulfate
8. concentrationconcentrated under reduced pressure

ORD record

ord-3f28c6a930864b58a2f5702306a7dbf1

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06265575B1