Trifluoroacetic acid → HCID 59383091, compound

HRID 913155Notes

Reaction equation

HRID 913155 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14](C(OC(C)(C)C)=O)[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]#[N:24])=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:16]=[CH:17][C:18]([O:21][CH2:22][C:23]#[N:24])=[CH:19][CH:20]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 67400969HCID 67400969, compound

Product 1

HCID 59383091HCID 59383091, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-[tert-butoxycarbonyl-(5-cyanomethoxy-pyridin-2-yl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (0.90 g, 2.1 mmol, 1.0 equiv) in dichloromethane (15 mL) was added 90% trifluoroacetic acid (1.69 mL, 2.37 g, 19 mmol, 9.0 equiv) drop by drop and the reaction mixture stirred at rt for 16 h. It was then poured into ice water and the pH adjusted to 9-10 by addition of a sat. solution of potassium carbonate. The solution was extracted three times with a mixture of dichloromethane/isopropanol (4:1). The combined organic layers were concentrated by evaporation under reduced pressure to give 0.15 g (30%) of the title compound as yellow oil. MS (ISP): 233.0 [M+H]+.

Workup

  1. extractionThe solution was extracted three times
  2. additionwith a mixture of dichloromethane/isopropanol (4:1)
  3. concentrationThe combined organic layers were concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-4b56eeeb4c4841fc90e43b5dd3990d04
Source dataset
uspto-grants-2011_09
Patent number
US08026255B2

Reaction notes

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