Trifluoroacetic acid → HCID 59191541, compound

HRID 1479980Notes

Reaction equation

HRID 1479980 reaction equation
[CH2:1]([C:8]1[N:13]=[N:12][C:11]([N:14]2[CH2:19][CH2:18][C:17]([OH:38])([C:20]3[CH:25]=[CH:24][C:23]([C:26]([CH3:37])([O:28]COCC[Si](C)(C)C)[CH3:27])=[CH:22][N:21]=3)[CH2:16][CH2:15]2)=[C:10]([CH3:39])[C:9]=1[CH3:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([C:8]1[N:13]=[N:12][C:11]([N:14]2[CH2:15][CH2:16][C:17]([OH:38])([C:20]3[CH:25]=[CH:24][C:23]([C:26]([OH:28])([CH3:37])[CH3:27])=[CH:22][N:21]=3)[CH2:18][CH2:19]2)=[C:10]([CH3:39])[C:9]=1[CH3:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59191606HCID 59191606, compound

Product 1

HCID 59191541HCID 59191541, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To compound 35 (44 mg, 0.078 mol) in CH2Cl2 (1.5 mL) at 0° C. is added TFA (0.15 μL). The mixture is stirred at 0° C. for 2 h and is quenched with 25% ammonium acetate, extracted with ethyl acetate. The organic phase is washed with brine, dried and concentrated to give a yellow residue which is purified by silica gel chromatography (0-5% methanol in CH2Cl2) to give the desired product (17 mg, 50%).

Workup

  1. customis quenched with 25% ammonium acetate
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give a yellow residue which
  7. customis purified by silica gel chromatography (0-5% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-9107bbac84294931a17af04cc91bf7d6
Source dataset
uspto-grants-2016_08
Patent number
US09409871B2

Reaction notes

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