Ammonium Chloride → tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-hydroxy-3-(tetrahydrofuran-3-yl)propanoate

HRID 56776

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HRID 56776 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:25]#[N:26])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:10](=[O:24])[CH:9]=2)[CH:7]=1.[O:27]1[CH2:31][CH2:30][CH:29]([CH:32]=[O:33])[CH2:28]1.[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:25]#[N:26])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH:32]([OH:33])[CH:29]3[CH2:30][CH2:31][O:27][CH2:28]3)[C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C:10](=[O:24])[CH:9]=2)[CH:7]=1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 1575683-Furancarboxaldehyde, tetrahydro-HCID 117622654tert-Butyl [4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]acetate

생성물 1

HCID 117622815tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-hydroxy-3-(tetrahydrofuran-3-yl)propanoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-70 °C

실험 절차

At −70° C., 6.94 ml (6.94 mmol, 1.3 eq.) of bis(trimethylsilyl)lithium amide (1M in THF) were added dropwise to a solution of 2.00 g (5.34 mmol) of tert-butyl [4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]acetate in 50 ml of tetrahydrofuran, the mixture was stirred at −70° C. for 10 min, a solution of 801 mg (8.00 mmol, 1.5 eq.) of tetrahydrofuran-3-carbaldehyde in 4 ml of tetrahydrofuran was added and the mixture was stirred at −70° C. for 90 min. The reaction mixture was warmed to −20° C., and 25 ml of semisaturated aqueous ammonium chloride solution were added. After phase separation, the aqueous phase was extracted with diethyl ether. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried (sodium sulphate), filtered, concentrated under reduced pressure and dried. The crude product was purified by flash chromatography (KP-SIL, petroleum ether/ethyl acetate 33-75%). Yield: 1.49 g (56% of theory)

후처리

  1. stirringthe mixture was stirred at −70° C. for 90 min
  2. temperatureThe reaction mixture was warmed to −20° C.
  3. customAfter phase separation
  4. extractionthe aqueous phase was extracted with diethyl ether
  5. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  6. dry with materialdried (sodium sulphate)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customdried
  10. customThe crude product was purified by flash chromatography (KP-SIL, petroleum ether/ethyl acetate 33-75%)

출처 및 근거

ORD 기록
ord-0cf31789b7f54dc1966a2a6529fe8676
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434690B2

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