1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → [2-(3-Fluoro-phenyl)-ethoxy]-acetic acid methyl ester

HRID 2100503Notes

Reaction equation

HRID 2100503 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][O:10][CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][CH:7]=1.[CH3:15]CN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CO.C(Cl)Cl>[CH3:15][O:13][C:12](=[O:14])[CH2:11][O:10][CH2:9][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 247694442-[2-(3-Fluorophenyl)ethoxy]acetic acid

Product 1

HCID 67099252[2-(3-Fluoro-phenyl)-ethoxy]-acetic acid methyl esterYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of [2-(3-fluoro-phenyl)-ethoxy]-acetic acid (1.20 g, 6.05 mmol), EDCI (1.28 g, 6.66 mmol), HOBt (0.90 g, 6.66 mmol) and DIPEA (1.56 ml, 9.08 mmol) in methanol (4 ml) was stirred at 0° C. for 2 hours. The reaction mixture was brought to dryness, dissolved in CH2Cl2 and washed twice with 1M NaOH and brine. The organic layers were dried over MgSO4, filtrated, the solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel, EtOAc/heptane, 1/4) to yield [2-(3-fluoro-phenyl)-ethoxy]-acetic acid methyl ester (1.20 g, 5.6 mmol; 93%) as colorless liquid. MS (m/e): 213.2 [M+H]+.

Workup

  1. washwashed twice with 1M NaOH and brine
  2. dry with materialThe organic layers were dried over MgSO4
  3. filtrationfiltrated
  4. customthe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography (silica gel, EtOAc/heptane, 1/4)

Sources & evidence

ORD record
ord-af11832e814f4a2cab5def56bac7df07
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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