Trifluoroacetic acid → HCID 23144637, compound

HRID 1967843Notes

Reaction equation

HRID 1967843 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([NH:17][C:18]2[S:19][C:20]([C:28]([CH:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[O:29])=[C:21]([C:23]3[O:24][CH:25]=[CH:26][CH:27]=3)[N:22]=2)=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[O:24]1[CH:25]=[CH:26][CH:27]=[C:23]1[C:21]1[N:22]=[C:18]([NH:17][C:15](=[O:16])[CH2:14][N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[S:19][C:20]=1[C:28]([CH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)=[O:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23144471HCID 23144471, compound

Product 1

HCID 23144637HCID 23144637, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 560 (428 mg, 0.849 mmol) was dissolved in dichloromethane (3 mL), and trifluoroacetic acid (3 mL) was added thereto at 0° C., followed by stirring at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and a saturated aqueous solution of sodium hydrogencarbonate was added to the resulting residue, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was reslurried with diethyl ether to afford the entitled Compound 561 (263 mg, 77%).

Workup

  1. customat 0° C.
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiona saturated aqueous solution of sodium hydrogencarbonate was added to the resulting residue
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-393483da409543599013845eb1caff60
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

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