Trifluoroacetic acid → Trifluoroacetic acid

HRID 2275515Notes

Reaction equation

HRID 2275515 reaction equation
C([O:5][C:6](=[O:24])[CH2:7][CH2:8][C:9]1[CH:22]=[CH:21][C:20]2[C:11](=[C:12]([NH2:23])[C:13]3[C:18]([N:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]=1)(C)(C)C.[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28]>ClCCl.C(OCC)C>[NH2:23][C:12]1[C:13]2[C:18]([N:19]=[C:20]3[C:11]=1[CH:10]=[C:9]([CH2:8][CH2:7][C:6]([OH:24])=[O:5])[CH:22]=[CH:21]3)=[CH:17][CH:16]=[CH:15][CH:14]=2.[C:27]([OH:29])([C:26]([F:31])([F:30])[F:25])=[O:28]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86634101HCID 86634101, compound

Product 2

HCID 6422Trifluoroacetic acidYield 76%HCID 57859223HCID 57859223, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

3-(9-Amino-acridin-2-yl)-propionic acid tert-butyl ester 7 (55 mg, 0.17 mmol) was dissolved in anhydrous dichloromethane (2 mL) and trifluoroacetic acid (2 mL) was carefully added. The mixture was stirred at room temperature overnight before evaporation of the solvent. Co-evaporation with diethyl ether (3 times) afforded a yellow solid, which was slurried in diethyl ether, filtered and washed with diethyl ether. Pure 3-(9-amino-acridin-2-yl)-propionic acid (Target 1) was isolated as a yellow TFA salt (49 mg, 76%). 1H NMR and LCMS analyses conformed to structure.

Workup

  1. customCo-evaporation with diethyl ether (3 times)
  2. customafforded a yellow solid, which
  3. filtrationfiltered
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-b66081676db145c68ecbca3c615323eb
Source dataset
uspto-grants-2015_09
Patent number
US09127164B2

Reaction notes

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