Triphenylphosphine → tert-butyl (6S,7S)-7-(4-chloro-3-fluorophenyl)-6-[(3-cyanopyridin-2-yl)oxy]-1,4-oxazepane-4-carboxylate

HRID 1022831노트

반응식

HRID 1022831 반응식
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C@@H:22]2[O:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24][C@H:23]2[OH:36])=[CH:18][C:17]=1[F:37].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O=[C:58]1[C:63]([C:64]#[N:65])=[CH:62][CH:61]=[CH:60][NH:59]1>O1CCCC1.O>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C@@H:22]2[O:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])[CH2:24][C@@H:23]2[O:36][C:58]2[C:63]([C:64]#[N:65])=[CH:62][CH:61]=[CH:60][N:59]=2)=[CH:18][C:17]=1[F:37]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 5775433-Cyano-2-pyridoneHCID 66976341tert-butyl (6R,7S)-7-(4-chloro-3-fluorophenyl)-6-hydroxy-1,4-oxazepane-4-carboxylate

생성물 1

HCID 66976656tert-butyl (6S,7S)-7-(4-chloro-3-fluorophenyl)-6-[(3-cyanopyridin-2-yl)oxy]-1,4-oxazepane-4-carboxylate수율 64.3%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Diisopropyl azodicarboxylate (1.9 M in toluene, 0.69 mL) was added dropwise to a solution of tert-butyl (6R,7S)-7-(4-chloro-3-fluorophenyl)-6-hydroxy-1,4-oxazepane-4-carboxylate (300 mg), triphenylphosphine (340 mg) and 2-oxo-1,2-dihydropyridine-3-carbonitrile (160 mg) in tetrahydrofuran (10 mL), and the mixture was stirred at room temperature for 4 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (250 mg).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-ff26bb7785f54bb2bc00919d2c121f20
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722662B2

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