Sodium Iodide → [4-(4-tert-Butoxycarbonylaminobutyl)phenoxy]acetic acid methyl ester

HRID 252184Notes

Reaction equation

HRID 252184 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:29][C:30]([O:32][CH3:33])=[O:31]>CN(C=O)C.C(OCC)(=O)C>[CH3:33][O:32][C:30](=[O:31])[CH2:29][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:19])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 22592408tert-Butyl [4-(4-hydroxyphenyl)butyl]carbamate

Product 1

HCID 21031129[4-(4-tert-Butoxycarbonylaminobutyl)phenoxy]acetic acid methyl esterYield 100.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of [4-(4-hydroxyphenyl)butyl]carbamic acid tert-butyl ester 31 (1.00 g, 3.78 mmol), potassium carbonate (0.627 g, 4.54 mmol), sodium iodide (0.567 g, 3.78 mmol), and methyl bromoacetate (0.40 mL, 4.21 mmol) in anhydrous DMF (8 mL) was stirred at room temperature for 14 h. The reaction mixture was then diluted with ethyl acetate (100 mL) and hexanes (20 mL), washed with water (20 mL×4) and brine (30 mL), and concentrated under reduced pressure to afford the desired product 32 as a yellow oil (1.28 g, 100% yield) which was used for the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 1.40 (s, 9H), 1.41-1.65 (m, 4H), 2.49-2.60 (m, 2H), 3.02-3.16 (m, 2H), 3.79 (s, 3H), 4.45 (br s, 1H), 4.59 (s, 2H), 6.79 (d, 2H), 7.05 (d, 2H). m/z (ESI): 338 [C18H27NO5+H]+.

Workup

  1. washwashed with water (20 mL×4) and brine (30 mL)
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d5437cb8bf9c44d38cd6958c6e6f4be4
Source dataset
uspto-grants-2011_01
Patent number
US07868010B2

Reaction notes

Loading…