Sodium hydride → HCID 21993956, 화합물

HRID 1978495노트

반응식

HRID 1978495 반응식
COP([CH2:7][C:8](=[O:24])[CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)(OC)=O.[H-].[Na+].[N:27]1[CH:28]=[C:29]2[N:38]3[C:33](=[CH:34][CH:35]=[CH:36][C:37]=13)[S:32][C:31]([CH:39]=O)=[CH:30]2>C1(C)C=CC=CC=1.CN(C)C=O.O>[C:20]([O:19][C:17]([N:14]1[CH2:13][CH2:12][CH:11]([CH2:10][CH2:9][C:8](=[O:24])/[CH:7]=[CH:39]/[C:31]2[S:32][C:33]3[N:38]4[C:29](=[CH:28][N:27]=[C:37]4[CH:36]=[CH:35][CH:34]=3)[CH:30]=2)[CH2:16][CH2:15]1)=[O:18])([CH3:21])([CH3:22])[CH3:23]

참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 21993678HCID 21993678, 화합물HCID 219941445-Thia-1,8b-diazaacenaphthylene-4-carbaldehyde

생성물 1

HCID 21993956HCID 21993956, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매2회HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4.77 g (13.1 mM) of tert-butyl 4-[4-(dimethoxyphosphoryl)-3-oxobutyl]piperidine-1-carboxylate in 50 ml of toluene was added 0.48 g (12.0 mM) of a 60% suspension of sodium hydride in liquid paraffin at room temperature, and the mixture was stirred at the prevailing temperature for 2 hours. This reaction mixture was added to a solution of the above crude 5-thia-1,8b-diazaacenaphthylene-4-carbaldehyde in N,N-dimethylformamide (30 ml)-toluene (50 ml) with ice-cooling and the mixture was stirred at the prevailing temperature for 3 hours. This reaction mixture was poured in water and extracted with 3 portions of ethyl acetate. The organic layers were pooled and dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol : 9/1) to provide crude (E)-5-[1-(tert-butoxycarbonyl)piperidin-4-yl]-1-(5-thia-1,8b-diazaacenaphthylen-4-yl)-1-penten-3-one. This crude product was not purified but used as it was in the next reaction.

후처리

  1. temperaturecooling
  2. stirringthe mixture was stirred at the prevailing temperature for 3 hours
  3. extractionextracted with 3 portions of ethyl acetate
  4. dry with materialdried over MgSO4
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol : 9/1)

출처 및 근거

ORD 기록
ord-ec0688b82ac64bbab5639e994ede7f05
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06235731B1

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