Dicyclohexylcarbodiimide → 4-(2-Benzyloxyacetylamino)phenoxyacetic acid methyl ester

HRID 83813

반응식

HRID 83813 반응식
[CH3:1][O:2][C:3](=[O:13])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1.[CH2:14]([O:21][CH2:22][C:23](O)=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH3:1][O:2][C:3](=[O:13])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:23](=[O:24])[CH2:22][O:21][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][CH:7]=1

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 290301(Benzyloxy)acetic acidHCID 6422115Methyl(4-aminophenoxy)acetate

생성물 1

HCID 592539834-(2-Benzyloxyacetylamino)phenoxyacetic acid methyl ester수율 68.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a mixture of (4-aminophenoxy)-acetic acid methyl ester 3 (20 g, 110.5 mmol) and benzyloxy acetic acid (20.4 g, 123 mmol) in anhydrous dichloromethane (200 ml) under nitrogen atmosphere was added dropwise a solution of 1,3-dicyclohexyl carbo-diimide (63.2 g, 306 mmol) in anhydrous dichloromethane (80 ml) then stirred at room temp. for 12 hours. The solids were filtered off, the dichloromethane was washed with 5% sodium bicarbonate solution (100 ml), water (100 ml) added, and the solids dried over sodium sulphate and distilled to get crude 49. Crude 49 was purified by column chromatography on silica gel using benzene as eluant to get pure 49 (25 g, 68.9%) as a white powder with an m.p. between 76-77.5° C. 1H NMR (CDCl3) δ 3.82 (s, 3H, ester), 4.10 (s, 2H, CH2), 4.62 (s, 2H, CH2), 4.66 (s, 2H, CH2), 6.88 (d, 2H, Ar), 7.38 (m, 5H, Ar), 7.46 (d, 2H, Ar), 8.24 (bs, 1H, NH)

후처리

  1. filtrationThe solids were filtered off
  2. washthe dichloromethane was washed with 5% sodium bicarbonate solution (100 ml), water (100 ml)
  3. additionadded
  4. dry with materialthe solids dried over sodium sulphate
  5. distillationdistilled
  6. customto get crude 49
  7. customCrude 49 was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-c57186fa43784b8e8a50548a6a12cdb3
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846845B2

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