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

HRID 843322Notes

Reaction equation

HRID 843322 reaction equation
C(OC(=O)[NH:7][CH:8]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH:9]([OH:39])[CH2:10][N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17](=[O:38])[NH:18][CH:19]([CH2:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:12]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:32]1([CH2:31][CH2:30][CH2:29][CH:19]([NH:18][C:17]([CH:13]2[CH2:14][CH2:15][CH2:16][N:11]([CH2:10][CH:9]([OH:39])[CH:8]([NH2:7])[CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:12]2)=[O:38])[CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18727510(1-Benzyl-2-hydroxy-3-{3-[4-phenyl-1-(3-phenyl-propyl)-butylcarbamoyl]-piperidine-1-yl}-propyl)-carbamic acid tert-butyl ester

Product 1

HCID 187274631-(3-Amino-2-hydroxy-4-phenyl-butyl)-piperidine-3-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amideYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(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.

Workup

  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

Sources & evidence

ORD record
ord-5a97b2e353f1475b8fbe0a0d1e2ed51c
Source dataset
uspto-grants-2002_04
Patent number
US06376514B1

Reaction notes

Loading…