Triethylamine → HCID 69848869、化合物

HRID 352185ノート

反応式

HRID 352185 の反応式
[CH3:1][O:2][C:3](=[O:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)Br.C(N(CC)CC)C.[NH:20]1[CH2:25][CH2:24][S:23][CH2:22][CH2:21]1>O1CCCC1>[CH3:1][O:2][C:3](=[O:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[N:20]1[CH2:25][CH2:24][S:23][CH2:22][CH2:21]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 67164ThiomorpholineHCID 137806Benzeneacetic acid, alpha-bromo-, methyl ester

生成物 1

HCID 69848869HCID 69848869、化合物収率 97%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of racemic α-bromophenylacetic acid methyl ester, 5.0 g (22.0 mmol) in 120 mL of tetrahydrofuran was added 3.4 mL (22.0 mmol) of triethylamine and 6.7 g (66.0 mmol) of thiomorpholine. The reaction mixture was refluxed for four hours, cooled to ambient temperature and concentrated to dryness. The residue was partitioned between 20% isopropanol/chloroform and water. The mixture was washed with saturated sodium bicarbonate, washed with brine, dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography using a methanol/chloroform gradient as eluent. A second purification was performed using chloroform as eluent and was concentrated to dryness to yield 5.36 g (97%) of the desired mixture of isomers as a yellow oil. MS (ion spray) 252.1 (M+).

後処理

  1. temperatureThe reaction mixture was refluxed for four hours
  2. concentrationconcentrated to dryness
  3. customThe residue was partitioned between 20% isopropanol/chloroform and water
  4. washThe mixture was washed with saturated sodium bicarbonate
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by chromatography
  10. customA second purification
  11. concentrationwas concentrated to dryness

出典と根拠

ORDレコード
ord-5b333947eed948619e3d6d5cb274428b
出典データセット
uspto-grants-2004_06
特許番号
US06743794B2

反応ノート

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