Ethyl Acetate → (S)-tert-butyl 1-oxo-1-phenylpentan-2-ylcarbamate

HRID 13104

反応式

HRID 13104 の反応式
CON(C)[C:4](=[O:17])[C@@H:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:6][CH2:7][CH3:8].[C:19]1([Mg]Br)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+].C(OCC)(=O)C>C1COCC1>[O:17]=[C:4]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C@@H:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:6][CH2:7][CH3:8]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 9992774(S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopentan-2-ylcarbamateHCID 178418255HCID 178418255、化合物

生成物 1

HCID 59339674(S)-tert-butyl 1-oxo-1-phenylpentan-2-ylcarbamate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

In a 50 mL round-bottomed flask was (S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopentan-2-ylcarbamate (91d, 250 mg, 0.96 mmol) dissolved in THF (9.6 ml). Phenylmagnesium bromide (2.88 ml, 2.88 mmol) 1.0 M in THF was added. The reaction was stirred at r.t. for 5 h. The reaction was poured into a mixture of saturated ammonium chloride and ethyl acetate. The mixture was shaken and the layers separated. The water layer was washed twice with ethyl acetate. The combined organic layers were washed once with a small portion of water and dried over sodium sulphate. The solvent was evaporated and the crude product was purified by flash chromatography.

後処理

  1. customIn a 50 mL round-bottomed flask was
  2. stirringThe mixture was shaken
  3. customthe layers separated
  4. washThe water layer was washed twice with ethyl acetate
  5. washThe combined organic layers were washed once with a small portion of water
  6. dry with materialdried over sodium sulphate
  7. customThe solvent was evaporated
  8. customthe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-1ba14a93921b47a5b43504fa8549e008
出典データセット
uspto-grants-2010_06
特許番号
US07728030B2

関連ノート

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