Sodium Bicarbonate → HCID 57918960, compound

HRID 2266257Notes

Reaction equation

HRID 2266257 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][C@H:8]([C@@H:23]1[CH2:28][CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24]1)[C:9]1[CH:10]=[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=2)[C:12]([F:15])=[CH:13][CH:14]=1)(=[O:3])[CH3:2].C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:15][C:12]1[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=2)=[CH:10][C:9]([C@@H:8]([C@@H:23]2[CH2:28][CH2:27][CH2:26][NH:25][CH2:24]2)[CH2:7][CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 57918939HCID 57918939, compound

Product 1

HCID 57918960HCID 57918960, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

(S)-tert-butyl 3-((R)-4-acetamido-1-(6-fluoro-3′-methylbiphenyl-3-yl)butyl)piperidine-1-carboxylate (40 mg, 0.083 mmol) was dissolved in a solution of 20% (V/V) TFA/CH2Cl2 (3 mL). The reaction mixture was stirred at rt for 1 h (monitored by HPLC) and a solution of satd aq NaHCO3 was added dropwise to adjust the pH to 7-8. The resulting mixture was extracted with CH2Cl2 (3×5 mL) and the combined extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo to afford N—((R)-4-(6-fluoro-3′-methylbiphenyl-3-yl)-4-((S)piperidin-3-yl)butyl)acetamide (30 mg, 94%). MS (E/Z): 383 (M+H+).

Workup

  1. extractionThe resulting mixture was extracted with CH2Cl2 (3×5 mL)
  2. washthe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6eb440ec2569445d95bb86a3cc77de8e
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

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