Sodium Hydroxide → HCID 66571528, compound

HRID 529388Notes

Reaction equation

HRID 529388 reaction equation
FC(F)(F)C([N:5]([CH2:15][C@H:16]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])[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@H:16]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])[CH2:17]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86708280HCID 86708280, compound

Product 1

HCID 66571528HCID 66571528, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 3-((S)-3-((2,2,2-trifluoro-N-((1R,2S)-2-phenylcyclopropyl)acetamido)methyl)pyrrolidin-1-yl)propanoate (108 mg, 0.245 mmol) in methanol (3 mL) was added sodium hydroxide (6M, 0.5 mL, 3.00 mmol) and the mixture was stirred at r room temperature for 18 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 off-white solid.

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-1f0cbdcd6e70438995fa35758a52c1f4
Source dataset
uspto-grants-2016_05
Patent number
US09346840B2

Reaction notes

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