Sodium Hydroxide → HCID 68385163, compound

HRID 529373Notes

Reaction equation

HRID 529373 reaction equation
FC(F)(F)C([N:5]([CH2:15][C:16]1([C:22]([O:24]C)=[O:23])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.[OH-].[Na+]>CO>[C:9]1([C@@H:7]2[CH2:8][C@H:6]2[NH:5][CH2:15][C:16]2([C:22]([OH:24])=[O:23])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86708266HCID 86708266, compound

Product 1

HCID 68385163HCID 68385163, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-((2,2,2-trifluoro-N-(trans-2-phenylcyclopropyl)acetamido)methyl)piperidine-4-carboxylate (110 mg, 0.286 mmol) in methanol (2 mL) was added sodium hydroxide (6M, 0.5 mL, 3.00 mmol), and the mixture was stirred at room temperature for 30 h. The mixture was purified using reverse-phase HPLC. The fractions containing the product were combined, treated with 1N HCl and concentrated. The residue was dried under vacuum to give 51 mg of product (HCl salt) as white solid. MS: (M+H)+=275.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.23-1.33 (m, 1H), 1.60 (br. s., 1H), 1.87 (br. s., 2H), 2.10-2.21 (m, 2H), 2.54-2.64 (m, 1H), 3.04 (br. s., 3H), 3.17-3.30 (m, 2H), 3.40-3.55 (m, 2H), 7.10-7.40 (m, 5H).

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-ce86ecf999a8402e9be2c488b75a4707
Source dataset
uspto-grants-2016_05
Patent number
US09346840B2

Reaction notes

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