Ethyl Acetate → tert-butyl {(S)-1-benzyloxymethyl-2-[2-oxo-2-(3,4,5-trifluorophenyl)ethoxy]ethyl}carbamate

HRID 553956

反応式

HRID 553956 の反応式
[Mg].[CH2:2]([O:9][CH2:10][C@H:11]1[CH2:16][O:15][CH2:14][C:13](=[O:17])[N:12]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl-].[NH4+].C(OCC)(=O)C.Br[C:34]1[CH:39]=[C:38]([F:40])[C:37]([F:41])=[C:36]([F:42])[CH:35]=1>C(OCC)C.O1CCCC1>[CH2:2]([O:9][CH2:10][C@H:11]([NH:12][C:18](=[O:19])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:16][O:15][CH2:14][C:13](=[O:17])[C:34]1[CH:39]=[C:38]([F:40])[C:37]([F:41])=[C:36]([F:42])[CH:35]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

参加物

8

反応物 5

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 6114091-Bromo-3,4,5-trifluorobenzeneHCID 5462224MagnesiumHCID 67373012tert-butyl(S)-3-benzyloxymethyl-5-oxomorpholine-4-carboxylate

生成物 1

HCID 67373700tert-butyl {(S)-1-benzyloxymethyl-2-[2-oxo-2-(3,4,5-trifluorophenyl)ethoxy]ethyl}carbamate

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

To a suspension of magnesium (249 mg) in diethyl ether (5 mL), 1-bromo-3,4,5-trifluorobenzene (446 μL) was added dropwise at 40° C. over 10 minutes, and the reaction solution was stirred at 40° C. for one hour. This solution was added dropwise to a solution of tert-butyl (S)-3-benzyloxymethyl-5-oxomorpholine-4-carboxylate (1.1 g) in tetrahydrofuran (30 mL) at −40° C. over 10 minutes, and the reaction solution was stirred at −40° C. for one hour. A saturated ammonium chloride solution was added to the solution in small portions at −40° C., and the reaction solution was returned to room temperature. Ethyl acetate was added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate system) to obtain 952 mg of the title compound. The property values of the compound are as follows.

後処理

  1. additionwas added dropwise at 40° C. over 10 minutes
  2. stirringthe reaction solution was stirred at −40° C. for one hour
  3. customwas returned to room temperature
  4. customthe organic layer was separated
  5. washThe resulting organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate system)

出典と根拠

ORDレコード
ord-b00f983059444e94b4487444e0330f20
出典データセット
uspto-grants-2011_11
特許番号
US08048878B2

関連ノート

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