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

HRID 2076816노트

반응식

HRID 2076816 반응식
[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

참가 물질

7

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 24769444953786-95-3

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-6a1b498125b64f2abfa35e174679a1d2
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928106B2

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