Sodium Hydroxide → HCID 68385257, compound

HRID 529375Notes

Reaction equation

HRID 529375 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:18][N:19]([C@@H:26]2[CH2:28][C@H:27]2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)C(=O)C(F)(F)F)([C:14]([O:16]C)=[O:15])[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][C:11]([CH2:18][NH:19][C@@H:26]2[CH2:28][C@H:27]2[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)([C:14]([OH:16])=[O:15])[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 86708270HCID 86708270, compound

Product 1

HCID 68385257HCID 68385257, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 1-benzyl-4-((2,2,2-trifluoro-N-(trans-2-phenylcyclopropyl)acetamido)methyl)piperidine-4-carboxylate (68 mg, 0.143 mmol) in methanol (2 mL) was added sodium hydroxide (1M, 1 mL, 6.00 mmol), and the mixture was stirred at room temperature for 30 h. The mixture 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 29 mg of product (HCl salt) as white solid. MS: (M+H)+=365.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.14-1.39 (m, 1H), 1.67 (br. s., 1H), 1.96-2.10 (m, 2H), 2.18-2.39 (m, 2H), 2.61-2.74 (m, 1H), 2.86-3.03 (m, 2H), 3.08-3.24 (m, 2H), 3.59 (br. s., 1H), 4.22-4.50 (m, 2H), 7.11-7.39 (m, 5H), 7.46 (br. s., 3H), 7.62 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-9d5f398c66304ead8ffcbb77e689da72
Source dataset
uspto-grants-2016_05
Patent number
US09346840B2

Reaction notes

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