4-Nitrobenzoyl chloride → HCID 68762968, 화합물

HRID 2190005노트

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HRID 2190005 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]3)[CH2:9][N:8]([C:23]3[C:24]4[C@H:31]([CH3:32])[CH2:30][CH:29]([OH:33])[C:25]=4[N:26]=[CH:27][N:28]=3)[C:5]2=[CH:6][CH:7]=1.[N+:34]([C:37]1[CH:45]=[CH:44][C:40]([C:41](Cl)=[O:42])=[CH:39][CH:38]=1)([O-:36])=[O:35]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]3)[CH2:9][N:8]([C:23]3[C:24]4[C@H:31]([CH3:32])[CH2:30][C@@H:29]([O:33][C:41](=[O:42])[C:40]5[CH:39]=[CH:38][C:37]([N+:34]([O-:36])=[O:35])=[CH:45][CH:44]=5)[C:25]=4[N:26]=[CH:27][N:28]=3)[C:5]2=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 85024-Nitrobenzoyl chlorideHCID 69809362tert-butyl 5-chloro-1-((5R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4'-piperidine]-1'-carboxylate

생성물 1

HCID 68762968HCID 68762968, 화합물수율 23%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 516892Sodium Bicarbonate용매

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온도
0 °C

실험 절차

A solution of tert-butyl 5-chloro-1-((5R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (0.065 g, 0.14 mmol) and TEA (0.038 ml, 0.28 mmol) in DCM was cooled to about 0° C. To the mixture was added 4-nitrobenzoyl chloride (0.031 g, 0.17 mmol). The reaction was stirred at about 0° C. for about 5 minutes, then warmed to about room temperature and stirred for 1.5 hours. The reaction was diluted with DCM and saturated NaHCO3. The combined extracts were washed with brine, dried over MgSO4, filtered and concentrated. The crude residue was purified by column chromatography (30-50% EtOAc/Hexane) to yield tert-butyl 5-chloro-1-((5R,7R)-5-methyl-7-(4-nitrobenzoyloxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (0.020 g, 23%). LCMS (APCI+) m/z 620, 622 [M+H]+; Rt=4.65 min, and to yield tert-butyl 5-chloro-1-((5R,7S)-5-methyl-7-(4-nitrobenzoyloxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (0.029 g, 29%). LCMS (APCI+) m/z 620, 622 [M+H]+; Rt=4.66 min.

후처리

  1. temperaturewarmed to about room temperature
  2. stirringstirred for 1.5 hours
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by column chromatography (30-50% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-1aa4a1a53b0f4fcd925ffe58623b59b0
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324221B2

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