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

HRID 2076816ノート

反応式

HRID 2076816 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-6a1b498125b64f2abfa35e174679a1d2
出典データセット
uspto-grants-2011_04
特許番号
US07928106B2

反応ノート

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