Ethylbenzene → (2S,3S)-1-Acetoxy-3-(t-butoxycarbonylamino)-2-hydroxy-4-phenylbutane

HRID 651257ノート

反応式

HRID 651257 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C@H:10]([OH:13])[CH2:11]Cl)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:21]([O-:24])(=[O:23])[CH3:22].[K+].C(C1C=CC=CC=1)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[C:21]([O:24][CH2:11][C@@H:10]([OH:13])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:23])[CH3:22]

参加物

6

反応物 3

HCID 7500EthylbenzeneHCID 517044Potassium AcetateHCID 71466451,1-Dimethylethyl N-((1S,2S)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl)carbamate

生成物 1

HCID 11056398(2S,3S)-1-Acetoxy-3-(t-butoxycarbonylamino)-2-hydroxy-4-phenylbutane収率 45%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6342Acetonitrile溶媒

実験手順

A mixture composed of 2.0 mmol (0.599 g) of (2S,3S)-3-(t-butoxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane, 0.1 mmol (0.032 g) of tetrabutylammoniumbromide, 5.0 mmol (0.49 g) of potassium acetate and 10 ml of acetonitrile was stirred under reflux for 50 hours. Thereafter, the solvent was distilled off under reduced pressure, 20 ml of water and 20 ml of ethyl acetate were added, and the organic layer was separated, dried over sodium sulfate, filtered and concentrated under reduced pressure to give a crude product. Quantitative analysis was curried out by high performance liquid chromatography using ethylbenzene as an internal standard. Thus was obtained 0.289 g (45%) of the title compound.

後処理

  1. temperatureunder reflux for 50 hours
  2. distillationThereafter, the solvent was distilled off under reduced pressure, 20 ml of water and 20 ml of ethyl acetate
  3. additionwere added
  4. customthe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a crude product

出典と根拠

ORDレコード
ord-bf3a26b2fc394a9b81216f832935b558
出典データセット
uspto-grants-2001_08
特許番号
US06278002B1

反応ノート

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