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

HRID 1180766노트

반응식

HRID 1180766 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2e7c945452a44b5dbe56d6ed99610ada
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282512B2

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