Trifluoroacetic acid → HCID 86709613, compound

HRID 1424528Notes

Reaction equation

HRID 1424528 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:18]([C:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][CH:26]=3)[O:22][N:21]=2)=[O:19])[CH:15]2[CH2:17][CH2:16]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+].C([O-])([O-])=O.[Na+].[Na+]>ClCCl>[CH:15]1([N:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[C:18]([C:20]2[CH:24]=[C:23]([C:25]3[CH:26]=[CH:27][C:28]([C:31]#[N:32])=[CH:29][CH:30]=3)[O:22][N:21]=2)=[O:19])[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 73058026HCID 73058026, compound

Product 1

HCID 86709613HCID 86709613, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-{[5-(4-cyano-phenyl)-isoxazole-3-carbonyl]-cyclopropyl-amino}-piperidine-1-carboxylic acid tert-butyl ester (90 mg) and trifluoroacetic acid (0.20 mL) in dichloromethane (3 mL) is stirred for 3 h at room temperature. The reaction mixture is diluted with dichloromethane prior to the addition of 2 N aqueous NaOH solution (1.5 mL) and aqueous Na2CO3 solution. The resulting mixture is stirred vigorously for 10 min. The organic phase is separated and the aqueous phase is extracted with dichloromethane. The combined extracts are dried over MgSO4 and concentrated in vacuo to give the desired product. LC (method 4): tR=1.02 min; Mass spectrum (ESI+): m/z=337 [M+H]+.

Workup

  1. stirringThe resulting mixture is stirred vigorously for 10 min
  2. customThe organic phase is separated
  3. extractionthe aqueous phase is extracted with dichloromethane
  4. dry with materialThe combined extracts are dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6aaf792359c54f0d9c347dc979c8528a
Source dataset
uspto-grants-2015_01
Patent number
US08927726B2

Reaction notes

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