Trifluoroacetic acid → HCID 67227228, compound

HRID 2045130Notes

Reaction equation

HRID 2045130 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>[F:18][C:19]([F:24])([F:23])[C:20]([OH:22])=[O:21].[NH2:9][CH2:8][CH:5]1[CH2:6][CH2:7][C:2]([CH3:17])([OH:1])[CH2:3][CH2:4]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 86647903HCID 86647903, compound

Product 1

HCID 67227228HCID 67227228, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of EXAMPLE 555A (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 hours, additional trifluoroacetic acid (0.5 mL) was added. After an additional 4 hours, the reaction mixture 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 mixture of cis and trans isomers.

Workup

  1. stirringAfter stirring for 2 hours
  2. concentrationthe reaction mixture 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-fa988c5fae5f44ffb6f825dbcc466895
Source dataset
uspto-grants-2013_11
Patent number
US08586754B2

Reaction notes

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