Trifluoroacetic acid → Ethyl (6-aminohexanoyl)aminomethylsalicylate trifluoroacetate

HRID 362574Notes

Reaction equation

HRID 362574 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:16][CH2:17][O:18][C:19]1[C:20](=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:15])=O)(C)(C)C.[F:30][C:31]([F:36])([F:35])[C:32]([OH:34])=[O:33]>ClCCl>[F:30][C:31]([F:36])([F:35])[C:32]([OH:34])=[O:33].[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:16][CH2:17][O:18][C:19]1[C:20](=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53930957ethyl (N-tert-butoxycarbonyl-6-aminohexanoyl)aminomethylsalicylate

Product 1

HCID 86753722Ethyl (6-aminohexanoyl)aminomethylsalicylate trifluoroacetateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl (N-tert-butoxycarbonyl-6-aminohexanoyl)aminomethylsalicylate (0.58 & 1.41 mmoles) was dissolved in dichloromethane (5 mL) and the solution was cooled in an ice/water bath. Trifluoroacetic acid (5 mL) was added, and the reaction was allowed to warm to room temperature. After 2 hours, the reaction mixture was evaporated to dryness to give. the product as an oil, which was dried in vacuo over potassium hydroxide pellets to afford 0. 59 g (99% yield) of ethyl (6-aminohexanoyl)aminomethylsalicylate trifluoroacetate.

Workup

  1. temperaturethe solution was cooled in an ice/water bath
  2. customthe reaction mixture was evaporated to dryness
  3. customto give
  4. dry with materialthe product as an oil, which was dried in vacuo over potassium hydroxide pellets
  5. customto afford 0

Sources & evidence

ORD record
ord-a79861a59a314a8eaf1a79b457bae12a
Source dataset
uspto-grants-1999_02
Patent number
US05869623

Reaction notes

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