(Diethylamino)sulfur trifluoride → HCID 86692272, 화합물

HRID 1469798노트

반응식

HRID 1469798 반응식
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([F:13])[C:5]([CH2:14][NH:15][C:16](=[O:22])[C:17]([CH3:21])([CH3:20])[CH2:18]O)=[CH:4][CH:3]=1.C(N(S(F)(F)[F:29])CC)C>C1COCC1>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([F:13])[C:5]([CH2:14][NH:15][C:16](=[O:22])[C:17]([CH3:21])([CH3:20])[CH2:18][F:29])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 86692262HCID 86692262, 화합물

생성물 1

HCID 86692272HCID 86692272, 화합물수율 51.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ethyl 6-chloro-2-fluoro-3-((3-hydroxy-2,2-dimethylpropanamido)methyl)benzoate (Intermediate-59, step 1, 200 mg, 0.60 mmol) in THF (2 mL) was added diethylaminosulfur trifluoride (146 mg, 0.90 mmol) and the reaction mixture was stirred at rt for 12 h. Then the reaction mixture was quenched with water and was extracted with CHCl3. The organic layer was washed with brine, separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 0.104 g of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.32 (t, 1H), 7.44-7.36 (m, 2H), 4.47-4.29 (m, 6H), 1.33-1.29 (t, J=6.9 Hz, 3H), 1.14 (s, 6H).

후처리

  1. customThen the reaction mixture was quenched with water
  2. extractionwas extracted with CHCl3
  3. washThe organic layer was washed with brine
  4. customseparated
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-60c4ae4065d7497d9cfb4880775125e3
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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