Ethyl bromoacetate → [2-(2-Methanesulfonylamino-ethyl)-phenoxy]-acetic Acid Ethyl Ester

HRID 890757Notes

Reaction equation

HRID 890757 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH:10][S:11]([CH3:14])(=[O:13])=[O:12].N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40]>O.CN(C=O)C>[CH2:42]([O:41][C:39](=[O:40])[CH2:38][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH3:43]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 1859152-NaphthylalanineHCID 22246821N-[2-(2-hydroxy-phenyl)-ethyl]-methanesulfonamide

Product 1

HCID 53987382[2-(2-Methanesulfonylamino-ethyl)-phenoxy]-acetic Acid Ethyl EsterYield 13.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-[2-(2-hydroxy-phenyl)-ethyl]-methanesulfonamide (4.3 g, 20 mmol), Nal (1.2 g, 8.0 mmol), K2CO3 (6.07 g, 44 mmol), ethyl bromoacetate (3.34 g, 20 mmol), and DMF (70 mL) was stirred at room temperature for 24 h. The reaction was poured into water and the aqueous solution was extracted with CH2Cl2. The organic solution was washed with water (1×) followed by brine (1×). The organic solution was dried (MgSO4), filtered, and concentrated. Flash chromatography (hexanes to 7:3 hexanes:EtOAc) provided the title compound (800 mg). 1H NMR (400 MHz, CDCl3) δ 7.18 (m, 2H), 6.93 (t, 1H), 6.71 (d, 1H), 4.97 (m, 1H), 4.65 (s, 2H), 4.24 (q, 2H), 3.42 (m, 2H), 2.94 (t, 2H), 2.75 (s, 3H), 1.27 (t, 3H); MS 319 (M+18).

Workup

  1. extractionthe aqueous solution was extracted with CH2Cl2
  2. washThe organic solution was washed with water (1×)
  3. dry with materialThe organic solution was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2288cdf262ad475fb250a2ee11f1de81
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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