Ammonium Chloride → HCID 71000664, 화합물

HRID 1023431

반응식

HRID 1023431 반응식
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.[CH:21]1([C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:25])[CH2:23][CH2:22]1.[NH4+].[Cl-]>C1COCC1.O.CCOC(C)=O>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[C:12]([CH2:14][C:24]([CH:21]2[CH2:22][CH2:23]2)([OH:25])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

8

반응물 4

HCID 25517Ammonium ChlorideHCID 77029Cyclopropyl phenyl ketoneHCID 11063648tert-butyl N-(4-methylpyridin-2-yl)carbamateHCID 178418339Butyllithium

생성물 1

HCID 71000664HCID 71000664, 화합물수율 82.3%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

(4-Methyl-pyridin-2-yl)-carbamic acid tert-butyl ester (200 mg, 0.96 mmol) is dissolved in dry THF (10 mL) and it is cooled down to −78° C. After 1.6 M n-BuLi (3.0 mL, 4.8 mmol) is added at −78° C., the cooling bath is removed and the mixture is stirred at room temperature for 15 min. Then the reaction mixture is cooled down to −78° C. again and cyclopropyl-phenyl-methanone (0.68 mL, 4.8 mmol) is added. After the mixture is stirred for 30 min at −78° C., saturated NH4Cl aqueous solution (35 mL) is added and the reaction is warmed up to room temperature. EtOAc (70 mL) is added along with water (70 mL). The mixture is stirred for another 10 min and the aqueous layer is separated, extracted with EtOAc (2×35 ml). The organic layers are combined and concentrated to give the crude product. Purification by silica flash column chromatography using MeOH in DCM (gradient from 0% to 10%) affords 280 mg of the desired product.

후처리

  1. customthe cooling bath is removed
  2. temperatureThen the reaction mixture is cooled down to −78° C. again
  3. stirringAfter the mixture is stirred for 30 min at −78° C.
  4. temperaturethe reaction is warmed up to room temperature
  5. stirringThe mixture is stirred for another 10 min
  6. customthe aqueous layer is separated
  7. extractionextracted with EtOAc (2×35 ml)
  8. concentrationconcentrated
  9. customto give the crude product
  10. customPurification by silica flash column chromatography

출처 및 근거

ORD 기록
ord-74cea6fbb84e437e9ddb61a3993d0c1b
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722709B2

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