Sodium Bicarbonate → HCID 68713790, compound

HRID 451655Notes

Reaction equation

HRID 451655 reaction equation
[NH2:1][C:2](=[O:27])[CH2:3][O:4][CH:5]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:20]=1[F:26])[C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7]1.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:25][C:21]1[C:20]([F:26])=[C:19]([C@@H:5]([CH:6]2[CH2:11][CH2:10][CH2:9][NH:8][CH2:7]2)[O:4][CH2:3][C:2]([NH2:1])=[O:27])[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 68713956HCID 68713956, compound

Product 1

HCID 68713790HCID 68713790, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of (R)-tert-butyl 3-((2-amino-2-oxoethoxy)(3-chloro-2-fluorophenyl)methyl)piperidine-1-carboxylate (100 mg, 0.25 mmol) in 20% TFA/CH2Cl2 (5 mL) was stirred at 0° C. for 30 min. The solvent was neutralized by adding saturated NaHCO3, extracted three times with CH2Cl2 and dried over Na2SO4. Evaporation of the solvent gave (R)-2-((3-chloro-2-fluorophenyl)(piperidin-3-yl)methoxy)acetamide (72 mg, 0.24 mmol, 98%). MS (E/Z): 301 (M+H+)

Workup

  1. extractionextracted three times with CH2Cl2
  2. dry with materialdried over Na2SO4
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-ec2dcfa8073d451690d2fa51352120b6
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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