Triethylsilane → (S)-4-Benzyl-3-[(S)-3-(4-hydroxyphenyl)-2-(4-methylphenoxy)propionyl]oxazolidin-2-one

HRID 1268948ノート

反応式

HRID 1268948 の反応式
C([SiH](CC)CC)C.[CH2:8]([C@H:15]1[CH2:19][O:18][C:17](=[O:20])[N:16]1[C:21](=[O:40])[C@@H:22]([O:32][C:33]1[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=1)[C@H:23](O)[C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>FC(F)(F)C(O)=O>[CH2:8]([C@H:15]1[CH2:19][O:18][C:17](=[O:20])[N:16]1[C:21](=[O:40])[C@@H:22]([O:32][C:33]1[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=1)[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

4

反応物 2

HCID 12052TriethylsilaneHCID 69504636(S)-4-Benzyl-3-[(2S,3R)-3-hydroxy-3-(4-hydroxyphenyl)-2-(4-methylphenoxy)propionyl]oxazolidin-2-one

生成物 1

HCID 69504567(S)-4-Benzyl-3-[(S)-3-(4-hydroxyphenyl)-2-(4-methylphenoxy)propionyl]oxazolidin-2-one収率 85.3%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

Triethylsilane (24.0 ml) was added at room temperature to a solution of (S)-4-benzyl-3-[(2S,3R)-3-hydroxy-3-(4-hydroxyphenyl)-2-(4-methylphenoxy)propionyl]oxazolidin-2-one (8.15 g) obtained from Reference example 20(c) in trifluoroacetic acid (90 ml), then the mixture was stirred for 18 hours and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The ethyl acetate layer was washed successively with a saturated aqueous sodium hydrogencarbonate solution, a 1N aqueous solution of hydrochloric acid and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crystals were filtered off and washed with a mixed solvent of isopropyl ether and hexane to give the target compound (6.70 g) as colorless crystals.

後処理

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe ethyl acetate layer was washed successively with a saturated aqueous sodium hydrogencarbonate solution
  4. dry with materiala 1N aqueous solution of hydrochloric acid and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. filtrationThe obtained crystals were filtered off
  7. washwashed with a mixed solvent of isopropyl ether and hexane

出典と根拠

ORDレコード
ord-fa22073ed3724617974207b48c2255ca
出典データセット
uspto-grants-2007_04
特許番号
US07199139B2

反応ノート

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