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

HRID 83815ノート

反応式

HRID 83815 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-5bf6bdf87ac1408c9e664611c1cdaa75
出典データセット
uspto-grants-2014_09
特許番号
US08846845B2

反応ノート

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