Trifluoroacetic acid → HCID 53649209, compound

HRID 1789848Notes

Reaction equation

HRID 1789848 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([CH:21]([CH3:33])[CH:22]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:23][S:24][C:25](=[O:27])[CH3:26])[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[CH2:31]([O:30][C:28](=[O:29])[CH:22]([CH2:23][S:24][C:25](=[O:27])[CH3:26])[CH:21]([CH:18]1[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]1)[CH3:33])[CH3:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54472035HCID 54472035, compound

Product 1

HCID 53649209HCID 53649209, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (2 mL) was added to a solution of 4-(3-acetylsulfanyl-2-ethoxycarbonyl-1-methyl-propyl)-piperidine-1-carboxylic acid tert-butyl ester (0.17 g, 0.439 mmol) in methylene chloride (10 mL). The reaction was stirred for 90 min and concentrated under reduced pressure. The crude product was purified using HPLC (10→50% acetonitrile in water, 0.1% TFA) to give 2-acetylsulfanylmethyl-3-piperidin4-yl-butyric acid ethyl ester (101 mg, 54%) as the TFA salt.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product was purified

Sources & evidence

ORD record
ord-9261c70df4e7495e965dc2f338370af3
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

Loading…