Triethylamine → 2-[4-(2-Benzyloxyacetylamino)phenoxy]propionic acid methyl ester

HRID 83815노트

반응식

HRID 83815 반응식
[CH3:1][O:2][C:3](=[O:14])[CH:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)[CH3:5].C(N(CC)CC)C.[CH2:22]([O:29][CH2:30][C:31](Cl)=[O:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CC(C)=O>[CH3:1][O:2][C:3](=[O:14])[CH:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:31](=[O:32])[CH2:30][O:29][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:9][CH:8]=1)[CH3:5]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 177085Benzyloxyacetyl chlorideHCID 22060471Methyl 2-(4-aminophenoxy)propanoate

생성물 1

HCID 592539632-[4-(2-Benzyloxyacetylamino)phenoxy]propionic acid methyl ester수율 59.8%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a mixture of 2-(4-aminophenoxy)-propionic acid methyl ester 10 (20 grams, 102.5 mmol) and triethylamine (23 ml, 165 mmol) in acetone (120 ml) at 0° C. was added dropwise benzyloxy acetyl chloride (28 g, 152 mmol) followed by stirring at room temp for 12 hours. The solids were filtered off, acetone distilled off, and water (100 ml) added. Crude 51 was extracted into chloroform, washed with 5% sodium bicarbonate (2×100 ml) and water (200 ml), then dried over sodium sulphate and distilled. Crude 51 was purified by column chromatography on silica gel using benzene as eluant to get pure 51 (21 g, 59.8%) as a light brown powder with an m.p. between 67-70° C. IH NMR (CDCl3) δ 1.60 (d, 3H, CH3), 3.72 (s, 3H, Ester), 4.02 (s, 2H, CH2), 4.62 (s, 2H, CH2), 4.68 (q, 1H, CH), 6.76 (d, 2H, Ar), 7.30 (m, 5H, Ar), 7.42 (d, 2H, Ar), 8.18 (s, 1H, NH)

후처리

  1. filtrationThe solids were filtered off
  2. distillationacetone distilled off
  3. additionwater (100 ml) added
  4. extractionCrude 51 was extracted into chloroform
  5. washwashed with 5% sodium bicarbonate (2×100 ml) and water (200 ml)
  6. dry with materialdried over sodium sulphate
  7. distillationdistilled
  8. customCrude 51 was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-5bf6bdf87ac1408c9e664611c1cdaa75
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846845B2

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