1-Hydroxybenzotriazole → [2-(3-Fluoro-phenyl)-ethoxy]-acetic acid methyl ester

HRID 2076816Notes

Reaction equation

HRID 2076816 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.Cl.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 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 24769444953786-95-3

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), EDCl (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, the residue was dissolved in CH2Cl2 and was washed twice with 1M NaOH and brine. The organic layers were dried over MgSO4, filtered, the solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel, EtOAc/heptane, 1:4) to yield the title compound (1.20 g, 5.6 mmol; 93%) as colorless liquid. MS: m/e=213.2 [M+H]+.

Workup

  1. washwas washed twice with 1M NaOH and brine
  2. dry with materialThe organic layers were dried over MgSO4
  3. filtrationfiltered
  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-6a1b498125b64f2abfa35e174679a1d2
Source dataset
uspto-grants-2011_04
Patent number
US07928106B2

Reaction notes

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