Trifluoroacetic acid → rac-1-(3-{[Cyclopentyl(4-methoxypiperidin-1-yl)acetyl]amino}-4-fluorobenzyl)cyclopropanecarboxylic acid trifluoroacetate

HRID 626456Notes

Reaction equation

HRID 626456 reaction equation
[CH:1]1([CH:6]([N:28]2[CH2:33][CH2:32][CH:31]([O:34][CH3:35])[CH2:30][CH2:29]2)[C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:24]=[CH:25][C:26]=2[F:27])[CH2:13][C:14]2([C:17]([O:19]C(C)(C)C)=[O:18])[CH2:16][CH2:15]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39]>ClCCl>[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39].[CH:1]1([CH:6]([N:28]2[CH2:33][CH2:32][CH:31]([O:34][CH3:35])[CH2:30][CH2:29]2)[C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:24]=[CH:25][C:26]=2[F:27])[CH2:13][C:14]2([C:17]([OH:19])=[O:18])[CH2:15][CH2:16]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118106687rac-tert-Butyl 1-(3-{[cyclopentyl(4-methoxypiperidin-1-yl)acetyl]amino}-4-fluorobenzyl)cyclopropanecarboxylate

Product 1

HCID 118106516rac-1-(3-{[Cyclopentyl(4-methoxypiperidin-1-yl)acetyl]amino}-4-fluorobenzyl)cyclopropanecarboxylic acid trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20.1 mg (0.04 mmol) of rac-tert-butyl 1-(3-{[cyclopentyl(4-methoxypiperidin-1-yl)acetyl]amino}-4-fluorobenzyl)cyclopropanecarboxylate (Example 95A) were dissolved in 2.4 ml of 20% strength trifluoroacetic acid in dichloromethane and stirred at RT for 5 h. The mixture was then concentrated on a rotary evaporator and the residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% TFA, 10:90→95:5; run time 38 min). This gave 6.8 mg (30% of theory) of the title compound.

Workup

  1. concentrationThe mixture was then concentrated on a rotary evaporator
  2. customthe residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% TFA, 10:90→95:5; run time 38 min)

Sources & evidence

ORD record
ord-bd7cdcab3f1541c0b7d26d690946696f
Source dataset
uspto-grants-2016_04
Patent number
US09309198B2

Reaction notes

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