Dichloromethane → HCID 11618343, compound

HRID 2245598Notes

Reaction equation

HRID 2245598 reaction equation
C(Cl)Cl.C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][NH:18][C:19]([C:21]2[CH:22]=[C:23]([C:28]3[CH:33]=[CH:32][C:31]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH:30][CH:29]=3)[C:24]([Cl:27])=[CH:25][CH:26]=2)=[O:20])[CH2:13][CH2:12]1)=O)(C)(C)C.FC(F)(F)C(O)=O>O>[NH:11]1[CH2:12][CH2:13][CH:14]([CH2:17][NH:18][C:19]([C:21]2[CH:22]=[C:23]([C:28]3[CH:29]=[CH:30][C:31]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH:32][CH:33]=3)[C:24]([Cl:27])=[CH:25][CH:26]=2)=[O:20])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 58791136HCID 58791136, compound

Product 1

HCID 11618343HCID 11618343, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an oven dried 10 mL round bottom flask was added 5 mL of DCM, 20 mg (0.04 mmol) of 331, 1.5 mL trifluoroacetic acid (TFA), and 50 μL H2O. The reaction solution was stirred for 1 hour and quenched with 1 mL of saturated NaHCO3. The product was taken up in 20 mL of DCM and the organic solution further washed with water (3×15 mL) and dried over Na2SO4. The organic solution was rotary evaporated to provide 16.0 mg of the product as a pale tan oil (99.0% yield). 1H NMR 400 MHz DMSO-d6: δH 8.71 (1H, dd, J=2.7, 3.1 Hz), 8.48 (1H, br s), 8.07 (1H, br s), 7.90 (1H, s), 7.83-7.30 (10H, m); 3.28-1.16 (11H, m); MS (ES+) m/z 405 (M+H); HPLC (214 nm), rt 4.94 min, 99.8%.

Workup

  1. customTo an oven dried 10 mL round bottom flask
  2. customquenched with 1 mL of saturated NaHCO3
  3. washthe organic solution further washed with water (3×15 mL)
  4. dry with materialdried over Na2SO4
  5. customThe organic solution was rotary evaporated

Sources & evidence

ORD record
ord-690a67a41d4c4e9db2610325f8c26b05
Source dataset
uspto-grants-2010_03
Patent number
US07683097B2

Reaction notes

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