Trifluoroacetic acid methylene chloride → HCID 56849388, compound

HRID 1092808Notes

Reaction equation

HRID 1092808 reaction equation
[NH2:1][CH2:2][C@@H:3]1[C:8]([C:9](=[O:23])[N:10]([CH:20]2[CH2:22][CH2:21]2)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2[Cl:19])=[C:7]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][O:33][C:34]3[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][C:35]=3[Cl:41])=[CH:26][CH:25]=2)[CH2:6][CH2:5][N:4]1C(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[NH2:1][CH2:2][C@@H:3]1[C:8]([C:9]([N:10]([CH:20]2[CH2:22][CH2:21]2)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2[Cl:19])=[O:23])=[C:7]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][O:33][C:34]3[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][C:35]=3[Cl:41])=[CH:26][CH:25]=2)[CH2:6][CH2:5][NH:4]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 66590077HCID 66590077, compound

Product 1

HCID 56849388HCID 56849388, compoundYield 25%

Procedure

Into a 10 mL round bottom flask was added 19D (50 mg, 79 μmol) and 25% TFA/DCM (5 mL). The mixture was stirred at room temperature for 3 hours. Solvent was removed under vacuum and the residue was purified by preparatory LCMS to yield Compound 14 (25-80%). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.23-0.91 (m, 4H) 2.33 (m, 2H) 2.99 (br. s., 1H) 3.30-3.59 (m, 4H) 4.07-4.68 (m, 7H) 6.85-7.07 (m, 2H) 7.14-7.31 (m, 4H) 7.40-7.59 (m, 4H). ESI-MS:m/z 636.2 (M+H)+.

Workup

  1. customSolvent was removed under vacuum
  2. customthe residue was purified by preparatory LCMS

Sources & evidence

ORD record
ord-0a6d4546c3c54cb7b5250864431da756
Source dataset
uspto-grants-2012_03
Patent number
US08129538B1

Reaction notes

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