tert-Butyl bromoacetate → HCID 35590271, compound

HRID 1362802Notes

Reaction equation

HRID 1362802 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C@H:13]([CH3:17])[C:14]([OH:16])=[O:15])[CH:7]=[CH:6]2.C([O-])(O)=O.[Na+].Br[CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C@H:13]([CH3:17])[C:14]([O:16][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:15])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 156391NaproxenHCID 516892Sodium Bicarbonate

Product 1

HCID 35590271HCID 35590271, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2S)-2-(6-methoxy(2-naphthyl))propanoic acid (naproxen, 3 g, 13.0 mmol), NaHCO3 (1.4 g, 16.7 mmol) and tert-butyl bromoacetate (5.08 g, 26.0 mmol) in DMF (30 mL) was stirred at room temperature for 2 days and the solvent was evaporated under high vacuo. The residue was then diluted with CH2Cl2, the solvent removed by filtration and the residue was recrystallized from a mixture of CH2Cl2/EtOAc/Hex to give the title compound as a white solid in quantitative yield. Mp 85-86° C. 1H NMR (300 MHz, CDCl3) δ 7.69-7.70 (m, 3H), 7.43 (dd, J=1.6 and 8.6 Hz, 1H), 7.10-7.15 (m, 2H), 4.47 (ABq, JAB=15.7 Hz, ΔνAB=40.7 Hz, 2H), 3.97 (q, J=7.2 Hz, 1H), 3.90 (s, 3H), 1.63 (d, J=7.2 Hz, 3H), 1.42 (s, 9H). 13C NMR (75 MHz, CDCl3) δ 174.2, 166.9, 157.8, 135.4, 133.9, 129.5, 129.1, 127.3, 126.5, 126.3, 119.1, 105.8, 82.5, 61.7, 55.5, 45.3, 28.1, 18.8. Mass spectrum (API-TIS) m/z 345 (MH+), 362 (MNH4+).

Workup

  1. customthe solvent was evaporated under high vacuo
  2. additionThe residue was then diluted with CH2Cl2
  3. customthe solvent removed by filtration
  4. customthe residue was recrystallized from a mixture of CH2Cl2/EtOAc/Hex

Sources & evidence

ORD record
ord-a99e0eae6b19483f8ebb3e84122f14b1
Source dataset
uspto-grants-2011_02
Patent number
US07883714B2

Reaction notes

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