Sodium Hydroxide → HCID 66571535, compound

HRID 534213Notes

Reaction equation

HRID 534213 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([C@@H:22]2[CH2:24][C@H:23]2[C:25]2[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=2)C(=O)C(F)(F)F)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C@@H:22]2[CH2:24][C@H:23]2[C:25]2[CH:26]=[CH:27][C:28]([C:29]([OH:31])=[O:30])=[CH:32][CH:33]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86708260HCID 86708260, compound

Product 1

HCID 66571535HCID 66571535, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(trans-2-(N-((1-benzylpiperidin-4-yl)methyl)-2,2,2-trifluoroacetamido)cyclopropyl)benzoic acid (18 mg, 0.039 mmol) in methanol (1 mL) was added sodium hydroxide (1M, 0.5 mL, 0.500 mmol) and the mixture was stirred at room temperature for 2 h. The mixture was concentrated and the residue was purified using reverse-phase HPLC under the acidic conditions. The fractions containing the product were combined, treated with 1N HCl, and concentrated. The residue was dried under vacuum to give 9 mg of product (HCl salt) as off white solid. MS: (M+H)+=365.2. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.50 (q, 1H), 1.59-1.77 (m, 3H), 2.14 (br. s., 3H), 2.63-2.74 (m, 1H), 3.03-3.26 (m, 5H), 3.55 (br. s., 2H), 4.36 (s, 2H), 7.32 (d, J=8.34 Hz, 2H), 7.49-7.62 (m, 5H), 7.99 (d, J=8.34 Hz, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified
  3. additionThe fractions containing the product
  4. additiontreated with 1N HCl
  5. concentrationconcentrated
  6. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-c62bdf6b01f9494ca7718f36c9efe848
Source dataset
uspto-grants-2014_10
Patent number
US08853408B2

Reaction notes

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