Trifluoroacetic acid → N1-[2-(2-aminoethoxy)-4-methoxybenzoyl]-N2-(4-methoxybenzoyl)-1,2-benzenediamine trifluoroacetate

HRID 1445450Notes

Reaction equation

HRID 1445450 reaction equation
C(OC([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:13]=1[C:14]([NH:16][C:17]1[C:18]([NH:23][C:24](=[O:33])[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:15])=O)(C)(C)C.[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43]>>[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43].[NH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:13]=1[C:14]([NH:16][C:17]1[C:18]([NH:23][C:24](=[O:33])[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:15]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86628409N1-[2-[2-(tert-butoxycarbonylamino)ethoxy]-4-methoxybenzoyl]-N2-(4-methoxybenzoyl)-1,2-benzenediamine

Product 1

HCID 86628410N1-[2-(2-aminoethoxy)-4-methoxybenzoyl]-N2-(4-methoxybenzoyl)-1,2-benzenediamine trifluoroacetateYield 89%

Procedure

N1-[2-[2-(tert-Butoxycarbonylamino)ethoxy]-4-methoxybenzoyl]-N2-(4-methoxybenzoyl)-1,2-benzenediamine (124 mg, 231 μmol) was dissolved in 3 ml of neat trifluoroacetic acid (TFA) in a capped vial for 90 min at room temperature. The volatiles were removed in vacuo and the residue was resuspended in a few ml of toluene and re-evaporated. This step was repeated twice more with toluene and once with dichloromethane. The resulting white solid was dried under high vacuum to give 113 mg (89%) of N1-[2-(2-aminoethoxy)-4-methoxybenzoyl]-N2-(4-methoxybenzoyl)-1,2-benzenediamine trifluoroacetate as a solid white film.

Workup

  1. customThe volatiles were removed in vacuo
  2. customre-evaporated
  3. customThe resulting white solid was dried under high vacuum

Sources & evidence

ORD record
ord-5fbffb8d309a408a8ade9490bafe6d2c
Source dataset
uspto-grants-2010_02
Patent number
US07666866B2

Reaction notes

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