Trifluoroacetic acid → 1-[(4-Chloro-3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}phenyl)-(methoxy)methyl]cyclopropanecarboxylic acid

HRID 1475688Notes

Reaction equation

HRID 1475688 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:19][CH3:20])[C:9]2([C:12]([O:14]C(C)(C)C)=[O:13])[CH2:11][CH2:10]2)=[CH:4][C:3]=1[NH:21][C:22](=[O:37])[C@H:23]([C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)[C@@H:24]([CH3:29])[C:25]([F:28])([F:27])[F:26].C(O)(C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:19][CH3:20])[C:9]2([C:12]([OH:14])=[O:13])[CH2:10][CH2:11]2)=[CH:4][C:3]=1[NH:21][C:22](=[O:37])[C@H:23]([C:30]1[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=1)[C@@H:24]([CH3:29])[C:25]([F:28])([F:27])[F:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68006868tert-butyl 1-[(4-chloro-3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}phenyl)(methoxy)methyl]cyclopropanecarboxylate

Product 1

HCID 573444421-[(4-Chloro-3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}phenyl)-(methoxy)methyl]cyclopropanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

151 mg (0.269 mmol) of tert-butyl 1-[(4-chloro-3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}phenyl)(methoxy)methyl]cyclopropanecarboxylate (as diastereomer mixture) were dissolved in 2.9 ml of dichloromethane, and 1.0 ml of TFA was added at RT. After 30 min at RT, the reaction mixture was concentrated under reduced pressure and the residue was concentrated under reduced pressure. The crude product obtained in this manner was purified by RP-HPLC (mobile phase acetonitrile/water). This gave 87 mg (64% of theory) of the target compound.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. concentrationthe residue was concentrated under reduced pressure

Sources & evidence

ORD record
ord-feef6a714b224708909cfd7a3c60f556
Source dataset
uspto-grants-2015_04
Patent number
US09018258B2

Reaction notes

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