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Phosphorus oxychloride → Benzyl 5-(2-(4-bromo-2,6-dimethylphenoxy)acetamido)-2-(ethylsulfonyl)benzylcarbamate

HRID 735708
ノート
印刷プレビュー

反応式

HRID 735708 の反応式
[Br:1][C:2]1[CH:12]=[C:11]([CH3:13])[C:5]([O:6][CH2:7][C:8]([OH:10])=O)=[C:4]([CH3:14])[CH:3]=1.[NH2:15][C:16]1[CH:17]=[CH:18][C:19]([S:34]([CH2:37][CH3:38])(=[O:36])=[O:35])=[C:20]([CH:33]=1)[CH2:21][NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]([O:6][CH2:7][C:8]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([S:34]([CH2:37][CH3:38])(=[O:36])=[O:35])=[C:20]([CH:33]=2)[CH2:21][NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:10])=[C:11]([CH3:13])[CH:12]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24813Phosphorus oxychlorideHCID 7248362-(4-Bromo-2,6-dimethylphenoxy)acetic acidHCID 57842737HCID 57842737、化合物

生成物 1

HCID 57842885Benzyl 5-(2-(4-bromo-2,6-dimethylphenoxy)acetamido)-2-(ethylsulfonyl)benzylcarbamate収率 98%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a solution of 79A (100 mg, 0.386 mmol) and 28A (148 mg, 0.386 mmol) in 2 mL pyridine at −15° C., was added POCl3 (0.040 mL, 0.425 mmol), dropwise. The mixture was stirred at this temperature for 20 min, then was quenched with water. The mixture was diluted with EtOAc, washed with water (2×), 1N HCl, water, sat. NaHCO3 and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography to afford 222 mg (98%) of 79B as a colorless oil. MS (ESI) m/z 589.2 (M+H)+.

後処理

  1. customwas quenched with water
  2. additionThe mixture was diluted with EtOAc
  3. washwashed with water (2×), 1N HCl, water, sat. NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-0b7170529d054cb483a301c0922813a2
出典データセット
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07592331B2

反応ノート

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