Sodium Bicarbonate → HCID 59598517, compound

HRID 2266254Notes

Reaction equation

HRID 2266254 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][O:7][C@@H:8]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=1[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[CH:30]=1)[C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]1)(=[O:3])[CH3:2].C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:28][C:24]1[C:23]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[CH:30]=2)=[C:22]([C@@H:8]([C@@H:9]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)[O:7][CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])[CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 59598523HCID 59598523, compound

Product 1

HCID 59598517HCID 59598517, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of (3R)-tert-butyl 3-((R)-(2-acetamidoethoxy)(6-fluoro-3′-methylbiphenyl-2-yl)methyl)piperidine-1-carboxylate (80 mg) in 20% TFA/CH2Cl2 (5 mL) was stirred at 0° C. for 30 min. The solvent was neutralized by adding satd aq NaHCO3 and extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4 and evaporated to give N-(2-((R)-(6-fluoro-3′-methylbiphenyl-2-yl)((R)-piperidin-3-yl)methoxy)ethyl)acetamide (20 mg, 32%).

Workup

  1. extractionextracted with CH2Cl2 (3×)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-82afc7656b02490c892aa9b4e872d227
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

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