Trifluoroacetic acid → 2-Methyl-N-(5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-malonamic acid

HRID 2223303Notes

Reaction equation

HRID 2223303 reaction equation
C(O)(C(F)(F)F)=O.C([O:12][C:13](=[O:36])[CH:14]([CH3:35])[C:15]([NH:17][CH:18]1[C:24](=[O:25])[N:23]([CH3:26])[C:22]2[CH:27]=[CH:28][CH:29]=[CH:30][C:21]=2[C:20]2[CH:31]=[CH:32][CH:33]=[CH:34][C:19]1=2)=[O:16])(C)(C)C>ClCCl>[CH3:35][CH:14]([C:15]([NH:17][CH:18]1[C:24](=[O:25])[N:23]([CH3:26])[C:22]2[CH:27]=[CH:28][CH:29]=[CH:30][C:21]=2[C:20]2[CH:31]=[CH:32][CH:33]=[CH:34][C:19]1=2)=[O:16])[C:13]([OH:36])=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 690397662-methyl-N-(5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-malonamic acid tert-butyl ester

Product 1

HCID 210725002-Methyl-N-(5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-malonamic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

TFA (3 ml) was added to a solution of 2-methyl-N-(5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-malonamic acid tert-butyl ester (920 mg, 2.33 mmol) in dichloromethane (3 ml) and the mixture was stirred at r.t. overnight. The mixture was then taken up in more dichloromethane, washed with water, and dried (Na2SO4). After evaporation of the solvent, the title compound, MS: m/e=339.3 (M+H+), (580 mg, 73%) was obtained by chromatographic purification of the residue (silica gel, MeOH, CH2Cl2).

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-d21709661a514231a4501c2b10d3b97b
Source dataset
uspto-grants-2008_05
Patent number
US07375099B2

Reaction notes

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