Sodium Iodide → [4-(4-Benzyloxycarbonylaminobutyl)phenoxy]acetic acid ethyl ester

HRID 910730Notes

Reaction equation

HRID 910730 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>CN(C=O)C.O>[CH2:36]([O:35][C:33](=[O:34])[CH2:32][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][CH2:12][CH2:11][NH:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:22])=[CH:16][CH:17]=1)[CH3:37]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 11637991N-Cbz4-(4-hydroxyphenyl)butylamine

Product 1

HCID 21031128[4-(4-Benzyloxycarbonylaminobutyl)phenoxy]acetic acid ethyl esterYield 89.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of [4-(4-hydroxyphenyl)butyl]carbamic acid benzyl ester (2.0 g, 6.7 mmol), potassium carbonate (1.0 g, 7.3 mmol), sodium iodide (0.4 g, 2.7 mmol), and DMF (10 mL) was stirred for 30 minutes. A solution of ethyl bromoacetate (0.8 mL, 7.4 mmol) in DMF (10 mL) was added dropwise to the reaction. The reaction was further stirred at room temperature for 3 days, and then poured into water (200 mL). The product was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 1:5 ethyl acetate/hexanes, v/v) to provide the desired product 33 (2.3 g, 89%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.34 (t, 3H), 1.57 (m, 4H), 2.56 (t, 2H), 3.20 (q, 2H), 4.25 (q, 2H), 4.59 (s, 2H), 5.10 (s, 2H), 6.85 (d, 2H), 7.06 (d, 2H), 7.38 (m, 5H).

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography (silica gel, 1:5 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-3ccd2b6d73064eb189a7ae40d2dde2cc
Source dataset
uspto-grants-2011_09
Patent number
US08022210B2

Reaction notes

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