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

HRID 16347

反応式

HRID 16347 の反応式
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[C:4]([F:10])[CH:3]=1.[Mg].[C:12]([O:16][C:17]([N:19]1[C:24](=[O:25])[CH2:23][O:22][CH2:21][C@@H:20]1[CH2:26][O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[Cl-].[NH4+]>C(OCC)(=O)C.O1CCCC1.C(OCC)C>[C:12]([O:16][C:17](=[O:18])[NH:19][C@@H:20]([CH2:26][O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:21][O:22][CH2:23][C:24](=[O:25])[C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[C:4]([F:10])[CH:3]=1)([CH3:15])([CH3:13])[CH3:14]

参加物

8

反応物 4

HCID 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 3

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
40 °C

実験手順

1-Bromo-3,4,5-trifluorobenzene (446 μL) was dropwise added to a diethylether suspension (5 mL) of magnesium (249 mg) over 10 min at 40° C. The resulting reaction solution was stirred at 40° C. for 1 hr and then dropwise added to a tetrahydrofuran solution (30 mL) of (S)-3-benzyloxymethyl-5-oxomorpholine-4-carboxylic acid tert-butyl ester (1.1 g) over 10 min at −40° C. The resulting reaction solution was stirred at −40° C. for 1 hr, and a saturated ammonium chloride aqueous solution was gradually added dropwise thereto at −40° C. The resulting reaction solution was warmed up to room temperature, and then ethyl acetate was added thereto. The organic layer was separated, washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate system) to give 952 mg of the title compound. The physical property values of this compound were as follows:

後処理

  1. customThe resulting reaction solution
  2. customThe resulting reaction solution
  3. stirringwas stirred at −40° C. for 1 hr
  4. customat −40° C
  5. customThe resulting reaction solution
  6. temperaturewas warmed up to room temperature
  7. customThe organic layer was separated
  8. washwashed with saturated saline
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate system)

出典と根拠

ORDレコード
ord-1cfeb729204c45378d4035f81c16e13b
出典データセット
uspto-grants-2010_06
特許番号
US07737141B2

関連ノート

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