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Potassium Carbonate → (S)-ethyl 2-tert-butoxy-2-(5-(4-chlorophenyl)-2-(hydroxymethyl)-7-methylquinolin-6-yl)acetate

HRID 931768
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HRID 931768 반응식
C([O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][C:10]([CH3:34])=[C:11]([C@H:23]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:12]=2[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[N:7]=1)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO.O>[C:30]([O:29][C@@H:23]([C:11]1[C:12]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[C:13]2[C:8](=[CH:9][C:10]=1[CH3:34])[N:7]=[C:6]([CH2:5][OH:4])[CH:15]=[CH:14]2)[C:24]([O:26][CH2:27][CH3:28])=[O:25])([CH3:31])([CH3:32])[CH3:33]
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참가 물질

5

반응물 2

HCID 11430Potassium CarbonateHCID 86691980(S)-ethyl 2-(2-(acetoxymethyl)-5-(4-chlorophenyl)-7-methylquinolin-6-yl)-2-tert-butoxyacetate

생성물 1

HCID 68587089(S)-ethyl 2-tert-butoxy-2-(5-(4-chlorophenyl)-2-(hydroxymethyl)-7-methylquinolin-6-yl)acetate수율 62%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water
용매

실험 절차

To a stirred solution of (S)-ethyl 2-(2-(acetoxymethyl)-5-(4-chlorophenyl)-7-methylquinolin-6-yl)-2-tert-butoxyacetate (0.095 mmol) in methanol (2 mL) was added 2 M K2CO3 (0.5 mL, excess) at room temperature. The mixture was stirred at room temperature for 1 hour, diluted with water. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product (26 mg, 62%). LCMS-ESI+ (m/z): 442.2, 444.2 (M+H)+.

후처리

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-9a03ac812aa84a31ab46c22b6487726b
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09296758B2

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