Trifluoroacetic acid → Trifluoroacetic acid

HRID 574967Notes

Reaction equation

HRID 574967 reaction equation
[OH:1][C:2]1([CH3:17])[CH2:7][CH2:6][CH:5]([CH2:8][NH:9]C(=O)OC(C)(C)C)[CH2:4][CH2:3]1.[F:18][C:19]([F:24])([F:23])[C:20]([OH:22])=[O:21]>ClCCl.O>[NH2:9][CH2:8][CH:5]1[CH2:6][CH2:7][C:2]([CH3:17])([OH:1])[CH2:3][CH2:4]1.[F:18][C:19]([F:24])([F:23])[C:20]([OH:22])=[O:21]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 86647903HCID 86647903, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 13574691HCID 13574691, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of EXAMPLE 376A (0.75 g) in dichloromethane (3 mL) was added a few drops of water followed by trifluoroacetic acid (1.19 mL) and the reaction stirred at room temperature. After stirring for 2 h added additional trifluoroacetic acid (0.5 mL). After an additional 4 h the reaction was concentrated and dried under high vacuum. The resulting oily solid was triturated with diethyl ether with sonication. Filtration and washing with diethyl ether gave the title compound as a trifluoroacetic acid salt and a mixture of cis and trans isomers.

Workup

  1. stirringAfter stirring for 2 h
  2. concentrationAfter an additional 4 h the reaction was concentrated
  3. customdried under high vacuum
  4. customThe resulting oily solid was triturated with diethyl ether with sonication
  5. filtrationFiltration
  6. washwashing with diethyl ether

Sources & evidence

ORD record
ord-66ee74b314f64fa5857061365dafb6d2
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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