Ethyl Acetate → 2-{1-[(Benzyloxy)methyl]cyclobutyl}ethanethioamide

HRID 1180766ノート

反応式

HRID 1180766 の反応式
[CH2:1]([O:8][CH2:9][C:10]1([CH2:14][C:15]#[N:16])[CH2:13][CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([S:19]P([O-])(OCC)=S)C.C(OCC)(=O)C>O1CCCC1.O>[CH2:1]([O:8][CH2:9][C:10]1([CH2:14][C:15](=[S:19])[NH2:16])[CH2:11][CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 11148614{1-[(Benzyloxy)methyl]cyclobutyl}acetonitrileHCID 53249491Diethyldithiophosphate

生成物 1

HCID 112651762-{1-[(Benzyloxy)methyl]cyclobutyl}ethanethioamide収率 71.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 9.7 g (45 mmol) of {1-[(benzyloxy)methyl]cyclobutyl}acetonitrile in 100 mL of tetrahydrofuran and 10 mL of water was added 15.13 mL (90.2 mmol) of diethyldithiophosphate and the contents heated at reflux for 16 h. Ethyl acetate and water were added, and the layers separated. The organic phase was dried using magnesium sulfate and concentrated under vacuum to afford the crude product, which was purified by silica gel chromatography using ethyl acetate:hexane (2:8) as the eluent to afford 8.0 g (71%) of 2-{1-[(benzyloxy)methyl]cyclobutyl}ethanethioamide as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 8.00 (br s, 2H), 7.39-7.30 (m, 5H), 4.59 (s, 2H), 3.58 (s, 2H), 3.09 (s, 2H), 2.14-1.87 (m, 6H).

後処理

  1. temperaturethe contents heated
  2. temperatureat reflux for 16 h
  3. customthe layers separated
  4. customThe organic phase was dried
  5. concentrationconcentrated under vacuum
  6. customto afford the crude product, which
  7. customwas purified by silica gel chromatography

出典と根拠

ORDレコード
ord-2e7c945452a44b5dbe56d6ed99610ada
出典データセット
uspto-grants-2007_10
特許番号
US07282512B2

反応ノート

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