Trifluoroacetic acid → 1-(3-Amino-2-hydroxy-4-phenyl-butyl)-piperidine-3-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide

(1-Benzyl-2-hydroxy-3-{3-[4-phenyl-1-(3-phenyl-propyl)-butylcarbamoyl]-piperidine-1-yl}-propyl)-carbamic acid tert-butyl ester (19) (194.4 mg; 0.3 mmol) is dissolved in methylene chloride (5 mL) at ambient temperature. Trifluoroacetic acid (5 mL) is added in a slow stream, and the solution is stirred for 90 minutes at ambient temperature. The solution is concentrated in vacuo at 40° C. The residue is slurried in a mixture of methylene chloride (10 mL) and water (100 mL), then potassium carbonate is added until the slurry is alkaline. The slurry is diluted with water (50 mL) then extracted with methylene chloride (3×50 mL). The organic extracts are dried over MgSO4, filtered, and concentrated in vacuo affording the desired product (150 mg) as an oil.

1. concentrationThe solution is concentrated in vacuo at 40° C
2. additionThe residue is slurried in a mixture of methylene chloride (10 mL) and water (100 mL)
3. additionpotassium carbonate is added until the slurry
4. additionThe slurry is diluted with water (50 mL)
5. extractionthen extracted with methylene chloride (3×50 mL)
6. dry with materialThe organic extracts are dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-14a6c6a026854fbd8eef985dd6f0b81a

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07135483B2