Dichloromethane → HCID 58791097, compound

HRID 2245599Notes

Reaction equation

HRID 2245599 reaction equation
C(Cl)Cl.C(OC(=O)[NH:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([C:17]1[CH:18]=[C:19]([C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:26][CH:25]=2)[C:20]([Cl:23])=[CH:21][CH:22]=1)=[O:16])(C)(C)C.FC(F)(F)C(O)=O>O>[NH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([C:17]1[CH:18]=[C:19]([C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:26][CH:25]=2)[C:20]([Cl:23])=[CH:21][CH:22]=1)=[O:16]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 58791129HCID 58791129, compound

Product 1

HCID 58791097HCID 58791097, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an oven dried 10 mL round bottom flask was added 5 mL of DCM, 10 mg (0.022 mmol) of 328, 1.5 mL trifluoroacetic acid (TFA), and 50 μL H2O. The solution was stirred for 1 hour and quenched with 1 mL of saturated NaHCO3. The product was taken up in 10 mL of DCM and washed with (3×5 mL) H2O and dried over Na2SO4. The organic solution was rotary evaporated to leave 5.9 mg of a pale yellow oil (73.6% yield). MS (ES+) m/z 365 (M+H); HPLC (214 nm), rt 7.06 min, 99.8%.

Workup

  1. customTo an oven dried 10 mL round bottom flask
  2. customquenched with 1 mL of saturated NaHCO3
  3. washwashed with (3×5 mL) H2O
  4. dry with materialdried over Na2SO4
  5. customThe organic solution was rotary evaporated

Sources & evidence

ORD record
ord-8e83b249676b4d5987222997af069430
Source dataset
uspto-grants-2010_03
Patent number
US07683097B2

Reaction notes

Loading…